Tag: M.W:100-200

Application of 3112-31-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3112-31-0 as follows.

General procedure: Pyrazole-3,5-dicarboxylic acid (0.348 g, 2 mmol) and0.168 g piperazine (2 mmol) were dissolved in 20 cm3distilled water. The mixture was stirred for 1 h at room temperature. Then metal salts, 0.291 g nickel(II) nitratehexahydrate (1 mmol) for 1 and 0.169 g manganese(II)sulfate tetrahydrate (1 mmol) for 2 were added into the above-mentioned solution. The reaction mixture was refluxed for 3 h. It was then gradually cooled to room temperature and kept until crystals suitable for X-ray diffraction were obtained.

According to the analysis of related databases, 3112-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sharif, Mahboubeh A.; Najafi, Gholam Reza; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1557 – 1563;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35100-92-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 35100-92-6 as follows.

6- (4 – ((2,5-dichloro-4-yl) amino) piperidin-1-yl) -3-cyano-pyridine (100mg, 0.286mmol) in n-butanol (5mL) solution of was added 1,5-dimethyl -1H- pyrazol-3-amine (40mg, 0.41mmol) and trifluoroacetic acid (212muL, 2.86mmol). The resultant reaction system was heated up to 120 deg.] C, sealed tube for 24 hours, until the reaction system was cooled to room temperature, concentrated under reduced pressure. To the resulting residue was added ethyl acetate (50 mL) was diluted and washed with water (15mL × 3) washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography Analysis (DCM / EtOAc / MeOH (v / v / v) = 25/5/1) to give the title compound as a whiteSolid (53mg, 44% yield)

According to the analysis of related databases, 35100-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (105 pag.)CN105461694; (2016); A;,
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Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 1-Methyl-1H-pyrazole-5-carboxylic acid

42-1 : 1 -Methyl-N-4-[rel-(4aS,5aS)-5a-methyl-4-oxo-3-(phenylamino)-1 ,4,4a,5,5a,6- hexahydrocyclopropa[f]indol-2-yl]pyridin-2-yl-1 H-pyrazole-5-carboxamide A solution of 1 -methyl-1 H-pyrazole-5-carboxylic acid (1 10 mg, 871 muiotaetaomicronIota) and HATU (331 mg, 871 muiotaetaomicronIota) in DMA (3 mL) was added to a mixture of rel-(4aR,5aR)-2-(2-Aminopyridin- 4-yl)-3-anilino-5a-methyl-4a,5,5a,6-tetrahydrocyclopropa[f]indol-4(1 H)-one (26; 100 mg, 290 muiotaetaomicronIota) and DIPEA (152 muIota_, 871 muiotaetaomicronIota) in DMA (3 mL) and stirred for 16 h at 50. The mixture was concentrated, DCM added and washed with water and dried over sodium sulfate. After filtration and concentration the residue was purified by Biotage (SNAP NH 28 g, EtOH:DCM) to give the title compound (91 mg, 69%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16034-46-1, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; GRAHAM, Keith; KLAR, Ulrich; BRIEM, Hans; SIEMEISTER, Gerhard; MOeNNING, Ursula; (145 pag.)WO2017/21348; (2017); A1;,
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Synthetic Route of 146941-72-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of N-(2′,4′-difluoro-5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-1-yl)-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide (100 mg, 0.181 mmol) in THF/EtOH/Water (5:5:2) was degassed by N2 bubbling for 5 min. 4-Bromo-1-methyl-1H-pyrazol-3-amine (35 mg, 0.19 mmol, 1.1 eq.) was added and the mixture was degassed for another 5 min. Bis(tri-tert-butylphosphine)palladium(0) (5 mg, 0.009 mmol, 0.05 eq.) and cesium carbonate (170 mg, 0.54 mmol, 3.0 eq.) were added sequentially and the mixture was further degassed for 5 min and heated at 90 C. for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to give the crude residue which was purified by preparative HPLC to give the product in 27% yield (25 mg). 1H NMR (300 MHz, DMSO): delta 10.3 (s, 1H) 8.79 (s, 1H), 7.95-7.92 (m, 2H), 7.77-7.07 (m, 2H), 7.59 (s, 2H), 7.53-7.47 (m, 3H), 7.29 (m, 1H), 3.75 (s, 3H), 2.91 (m, 1H), 1.5-1.49 (d, 2H), 1.30-1.26 (t, 2H), 1.03-1.01 (t, 2H); LC-MS (ESI): Calculated mass: 520.5; Observed mass: 521.0 [M+H]+ (rt: 0.676 min).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-methyl-1H-pyrazol-3-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Linnanen, Tero; Wohlfahrt, Gerd; Nanduri, Srinivas; Ujjinamatada, Ravi; Rajagopalan, Srinivasan; Mukherjee, Subhendu; US2015/11548; (2015); A1;,
Pyrazole – Wikipedia,
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Synthetic Route of 5334-40-7, These common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of EDC (4.81 g 25 mmol), HOBt (3.40 g, 25 mmol) and triethylamine (4.67 g, 46 mmol) in DMF (100 ml) was added 4-nitro-lH-pyrazole-3-carboxylic acid (3.63 g, 23.09 mmol) and 4,5-dimethoxy-benzene-l,2-diamine dihydrochloride (5.06g, 20.99 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the resulting solid partitioned between EtOAc (50 ml) and saturated aqueous NaHCO3 (50 ml). A precipitate was formed and removed by filtration. The filtrate was washed with water followed by diethyl ether and then azeotroped with MeOH and toluene to yield 4- nitro-lH-pyrazole-3- carboxylic acid (2-amino-4,5-dimethoxy-phenyl)- amide (2.35 g, 36percent). 4-Nitro- lH-pyrazole-3-carboxylic acid (2-amino-4,5-dimethoxy-phenyl)-amide (2.35g, 7.65 mmol) was dissolved in acetic acid (150 ml) and refluxed at 140° C for 5 hours. The solution was left to cool and the solvent removed in vacuo. The resulting solid was partitioned between EtOAc (25 ml) and brine (25 ml). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to yield 5,6- dimethoxy-2-(4-nitro-lH-pyrazol-3-yl)-lH-benzimidazol (2.08 g, 94percent).

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/70195; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3994-50-1

To tert-butyl N-[( iS)- 1 -(3 -bromo-5 -fluorophenyl)but-3 -en-i -yl] carbamate (0.19 g, 0.552 mmol), i-methyl-4-nitro-iH-pyrazole (0.070 g, 0.552 mmol), di(adamantan-i20 yl)(butyl)phosphine (0.059 g, 0.166 mmol), pivalic acid (0.019 ml, 0.166 mmol), K2C03(0.229 g, 1.656 mmol) was added DMF (1.1 ml), and the mixture was purged with Ar. Pd(OAc)2 (0.025 g, 0.110 mmol) was added and the reaction was heated at 120 C for 18 h. The reaction was partitioned between water (15 ml) and EtOAc (30 ml). The aqueous layer was extracted with EtOAc (2 x 20 ml). The combined organic layers was washedwith brine (15 ml), dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography using hexanes and EtOAc as eluents to give tert-butyl N- [(15)-i -[3 -fluoro-5 -(1 -methyl-4-nitro- iH-pyrazol-5 -yl)phenyl]but-3 -en-i -yl]carbamate (0.123 g, 57%) as a yellow oil. ?HNMR(400MHz, CDC13)oe 8.23- 8.i7(m, iH), 7.22-7.16 (m, 1H), 7.10 (s, 1H), 7.01 (dt,J=8.5, 1.9 Hz, 1H), 5.76-5.60 (m, 1H), 5.22-5.11(m, 2H), 4.90 (br. s., 1H), 4.78 (br. s., 1H), 3.78 – 3.69 (m, 3H), 2.60 – 2.48 (m, 2H), 1.41(br. s., 9H).

According to the analysis of related databases, 3994-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 89501-90-6, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89501-90-6 as follows.

EXAMPLE 5 1-Methylpyrazole-3-sulfonamide A mixture containing chloroform (100 ml), 13.6 g of 1-methylpyrazole-3-sulfonyl chloride and 13.6 g ammonium carbonate was heated to reflux for six hours, cooled, filtered and the solid was washed with water. The water-insoluble solid which was recrystallized from 50% ethanol-water melted at 149-151 and showed absorption peaks in the infrared at 3100 and 3200 cm-1, consistent for the NH2 in the desired product. Anal. Calc. for C4 H7 N3 O2 S: C, 29.8; H, 4.38; N, 26.07; S, 19.9. Found: C, 29.3; H, 4.6; N, 25.3; S, 19.2.

According to the analysis of related databases, 89501-90-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4931081; (1990); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1001020-14-9,Some common heterocyclic compound, 1001020-14-9, name is 3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C5H3F3N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

e) 2-(2-(4-Formyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl)acetamido)-N-(2-hydroxyethyl)- 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide2-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carboxamide (2.91 g, 8.06 mmol) was dissolved in DMF (25 ml.) and potassium carbonate (2.23 g, 16.11 mmol), followed by 3-(trifluoromethyl)-1 H-pyrazole-4-carbaldehyde (1.39 g, 8.46 mmol), added. The mixture was stirred at 60 0C for 25 min after which time the reaction mixture was diluted with water (-800 ml_), then acidified with 5 N HCI until pH 1. During acidification a free flowing solid was obtained which was collected by filtration. NMR analysis indicated ~60-70 % purity of desired product. The solid was succesfully triturated with a mixture of DCM/ether to give a light beige solid which was collected by filtration. The mother liquor was concentrated and a second batch obtained using a similar process. The batches were combined to yield the title product (1.76 g, 3.95 mmol, 49 %). MS (ESI) : m/z 443.5 [M – H]

The synthetic route of 1001020-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 138786-86-4 as follows. Application In Synthesis of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Preparation of tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate (I); A solution of methyl 4-nitro-1H-pyrazole-3-carboxylate (54.0 g, 315.6 mmol), phenylboronic acid (77.0 g, 631.2 mmol), copper(II) acetate (86.0 g, 473.4 mmol) and pyridine (49.9 g, 631.2 mmol) in methylene chloride (600 mL) was stirred at ambient temperature open to air for 48 hours. The reaction was evaporated in vacuo, diluted with 1000 mL methylene chloride and filtered through a large plug of silica (washing with 2 liters methylene chloride). The solvent was evaporated in vacuo. 1H NMR (CDCl3) delta 8.61 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 4.02 (s, 3H).

According to the analysis of related databases, 138786-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1260243-04-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1260243-04-6 name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example C.22 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid; a. A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160° C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0° C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52percent). White solid. MS (ISN) 316.3 [(M-H)-]; mp 190-192° C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-amino-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics