Category: 920006-32-2

Synthetic Route of 920006-32-2, These common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-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.

tert-Butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (240 mg, 0.67 mmol) obtained in Example 145-E) was dissolved in 12M hydrochloric acid (1 mL) and ethanol (1 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, basified with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (2 mL), 1-(1-methylethyl)-1H-pyrazole-5-carboxylic acid (104 mg, 0.67mmol)), HATU (307 mg, 0.81 mmol) and DIEA (0.058 mL, 0.34 mmol) were added at room temperature, and the mixture was stirred at 60C for 3 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (90:10-50:50)] to give the title compound (130 mg) as a pale-brown powder (yield 49%). MS (ESI+): [M+H]+ 393. 1H NMR (300 MHz, CDCl3) delta 1.51 (6H, d, J = 6.8 Hz), 2.40 (3H, s), 4.20 (2H, s), 5.30-5.65 (1H, m), 6.64 (1H, d, J = 2.3 Hz), 6.87-7.05 (2H, m), 7.11 (1H, s), 7.57 (1H d, J = 1.9 Hz), 7.72 (1H, brs).

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 1-Isopropylpyrazole-5-carboxylic Acid

DIPEA (94 pL, 0.57 mmol) was added to a stirred solution of Intermediate 56 (70 mg, 0.19 mmol), 1 -(propan-2-yl)- 17/-pyrazolc-5-carboxylic acid (44 mg, 0.28 mmol) and HATU (112 mg, 0.29 mmol) in DCM (2.5 mL) at r.t. The reaction mixture was stirred at r.t. for 18 h, then diluted with water (5 mL) and extracted with DCM (3 x 15 mL). The combined organic phases were separated using a hydrophobic PTLE frit, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, using a gradient of fc/7-butyl methyl ether in heptane (0-80%), to afford the title compound (61 mg, 65%) as a white solid. 5H (250 MHz, DMSO-de) 10.12 (s, 1H), 8.45 (d, J8.2 Hz,1H), 7.70-7.66 (m, 1H), 7.50 (d, 1.9 Hz, 1H), 7.43-7.33 (m, 2H), 7.12 (d, J5.6 Hz, 1H), 6.95 (d, 2.0 Hz, 1H), 6.81 (d, J5.7 Hz, 1H), 5.44-5.34 (m, 1H), 4.37 (t, j 8.5 Hz, 1H), 3.99-3.90 (m, 2H), 3.77-3.67 (m, 2H), 2.11-2.01 (m, 2H), 1.91-1.75 (m, 2H), 1.74-1.65(m, 2H), 1.63-1.56 (m, 1H), l.37 (d, 6.6 Hz, 3H), 1.34 (d, J6.6 Hz, 3H), 1.32-1.26 (m, 1H), 1.25-1.18 (m, 1H), 1.16-1.10 (m, 2H), 1.10-1.01 (m, 1H), 0.92-0.81 (m, 5H). uPLC- MS (method 1): MH+ m/z 491, RT 4.06 minutes.

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SRL; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; FOULKES, Gregory; LECOMTE, Fabien Claude; (0 pag.)WO2020/11731; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 920006-32-2, These common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-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.

Intermediate 941 -(1 -Methylethyl)-1 H-pyrazole-5-carbonyl chloride Thionyl chloride (5 ml) was added to 1-(1-methylethyl)-1 H-pyrazole-5-carboxylic acid (1g) and the reaction was heated at 800C for 5h. The reaction was evaporated, then azeotroped with toluene to give title compound, 856mg. 1H NMR (CDCI3) delta 7.6 (d, 1 H), delta 7.1 (d, 1 H), delta 5.2 (m, 1 H), delta 1.5 (d, 6H).

Statistics shows that 1-Isopropylpyrazole-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 920006-32-2.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147188; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 920006-32-2,Some common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, molecular formula is C7H10N2O2, 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.

1-(propan-2-yl)-1H-pyrazole-5-carboxylic acid (37.8 mg, 245 pmol), HATU (108 mg, 283 pmol), and N,N-diisopropylethylamine (99 mI, 570 mihoI), were dissolved in 3 mL of the N,N-dimethylformamide and the resulting mixture was stirred at room temperature for 15 min, then tert-butyl 3-amino-5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazole-1-carboxylate (100 mg, 85 % purity, 189 pmol) was added and the resulting mixture was stirred at 90 C for 16 h. The resulting mixtur e was diluted by addition of water and extracted with ethyl acetate, the combined organic phases was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by prep-HPLC (Column: XBridge Prep C18 OBD Column 19x150mm, 5 pm; Mobile Phase A: Water (10 mmol/L NH4HC03), Mobile Phase B: ACN; Flow rate: 20 mUmin; Gradient: 25% B to 65% B in 7 min; Detector: 254 nm, 220 nm) to give 39.9 mg (43% yield) of the product as a light yellow solid. LC-MS [Water(0.05%TFA)-Acetonitrile, 5%B]: Rt = 1 .38 min. MS (ESIpos): m/z = 487 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .24 (t, 3H), 1 .44 (d, 6H), 2.23 (s, 6H), 2.90 (q, 2H), 3.20 (s, 3H), 4.66 (s, 1H), 5.50-5.56 (m, 1H), 7.16 (s, 1H), 7.53-7.55 (m, 1H), 7.59 (s, 1H), 10.85 (s, 1H), 13.12 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Isopropylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; CHRIST, Clara; BRIEM, Hans; FARIA ALVARES DE LEMOS, Adelaide, Clara; BADER, Benjamin; HOLTON, Simon; BOeMER, Ulf; LIENAU, Philip; KUHNKE, Lara, Patricia; (122 pag.)WO2019/185525; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 920006-32-2, 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. 920006-32-2 name is 1-Isopropylpyrazole-5-carboxylic Acid, 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.

To a solution of HATU (0.253 g) in DMF (3 ml) was added 1 -(1 -methylethyl)-1 H-pyrazole- 5-carboxylic acid (0.102 g) and DIPEA (0.21 1 ml) and the mixure was left to stand for 10 min. 6-(1 H-lndol-4-yl)-1 H-indazol-4-amine (0.075 g) dissolved in DMF (3 ml) was added and the solution was left to stand at RT for 18 h. DMF was removed by blow down (not to dryness) and the residue was dissolved in chloroform (1 ml) and loaded onto an aminopropyl SPE (2 g) (pre-conditioned with methanol (6 ml) and chloroform (6 ml)). The mixure was left on the column for 2 h then eluted with ethyl acetate:methanol (1 :1 , 10 ml). The solvent was blown down to dryness and the residue was dissolved in DMSO:methanol (1 ml, 1 :1 ) and purified by MDAP (method A). The solvent was removed in vacuo and dried in an vacuum oven (50 C) overnight to give title compound, 18 mg. LCMS (method A) Rt = 3.23 min, MH+ = 385.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropylpyrazole-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian, Robert; DOWN, Kenneth, David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie, Nicole; LE, Joelle; LUNNISS, Christopher, James; PARR, Nigel, James; RITCHIE, Timothy, John; ROBINSON, John, Edward; SIMPSON, Juliet, Kay; SMETHURST, Christian, Alan, Paul; WO2011/67364; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 920006-32-2, category: pyrazoles-derivatives

Example 100 N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-1-(1-methylethyl)-1H-pyrazole-5-carboxamide To a solution of HATU (0.253 g) in DMF (3 ml) was added 1-(1-methylethyl)-1H-pyrazole-5-carboxylic acid (0.102 g) and DIPEA (0.211 ml) and the mixture was left to stand for 10 min. 6-(1H-Indol-4-yl)-1H-indazol-4-amine (0.075 g) dissolved in DMF (3 ml) was added and the solution was left to stand at RT for 18 h. DMF was removed by blow down (not to dryness) and the residue was dissolved in chloroform (1 ml) and loaded onto an aminopropyl SPE (2 g) (pre-conditioned with methanol (6 ml) and chloroform (6 ml)). The mixture was left on the column for 2 h then eluted with ethyl acetate:methanol (1:1, 10 ml). The solvent was blown down to dryness and the residue was dissolved in DMSO:methanol (1 ml, 1:1) and purified by MDAP (method K). The solvent was removed in vacuo and dried in an vacuum oven (50 C.) overnight to give title compound, 18 mg. LCMS (method B) R=3.23 mi MH=385.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropylpyrazole-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; Hamblin, Julie Nicole; Jones, Paul Spencer; Keeling, Suzanne Elaine; Le, Joelle; Mitchell, Charlotte Jane; Parr, Nigel James; (136 pag.)US9326987; (2016); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 920006-32-2,Some common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, molecular formula is C7H10N2O2, 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.

A mixture of 2-isopropylpyrazole-3-carboxylic acid (50 mg, 291.89 mumol, 1 eq), 2-methyl-4-[(E)-2-(o-tolyl) vinyl]aniline (93.12 mg, 291.89 mumol, 1 eq), T3P (1.86 g, 2.92 mmol, 1.74 mL, 50%, 10 eq) in pyridine (5 mL) was stirred at 60 C. for 2 h. The mixture was concentrated under reduced pressure to give a residue which was purified by preparative HPLC (column: Phenomenex Gemini 150*25 mm*10 um; mobile phase: [water(0.05% HCl)-ACN]; B %: 55%-85%, 10 min). The mixture was lyophilized, purified by preparative TLC (SiO2, PE/EtOAc=5/1, Rf=0.57) to give 2-isopropyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrazole-3-carboxamide (compound I-42, 18.26 mg, 48.58 mumol, 16.6% yield, 95.6% purity) as an off-white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.95 (d, J=8.0 Hz, 1H), 7.60-7.55 (m, 3H), 7.40-7.39 (m, 2H), 7.30 (d, J=16.0 Hz, 1H), 7.19-7.17 (m, 3H), 6.96 (d, J=16.0 Hz, 1H), 6.61 (s, 1H), 5.57-5.47 (m, 1H), 2.44 (s, 3H), 2.35 (s, 3H), 1.54 (d, J=6.8 Hz, 6H); ES-LCMS m/z 360.2 [M+H]+.

The synthetic route of 920006-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 920006-32-2, SDS of cas: 920006-32-2

The 2-Isopropyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide was prepared from 3-nitrobenzoyl chloride using the following multiple step procedure: Step 1: 2-Isopropyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide. A dry flask was charged with 2-Isopropyl-2H-pyrazole-3-carboxylic acid (0.159 g, 1.03 mmol) and thionyl chloride (5 mL) and allowed to stir at 79 C. for 3 h. The thionyl chloride was then removed by concentration in vacuo. The crude acid chloride was cooled to room temperature, and then dissolved in THF (101 mL). 6-(3-Amino-benzoyl)-1,3-dihydro-indol-2-one (as prepared in Example 40, 0.260 g, 1.03 mmol) was added to the THF solution of the acid chloride, and the mixture was allowed to reflux overnight. The reaction mixture was then allowed to cool to room temperature and filtered. The solid residue was washed with 0 C. THF and collected to afford the 2-Isopropyl-2H-pyrazole-3-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide as a solid (0.328 g, 0.84 mmol, 82%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropylpyrazole-5-carboxylic Acid, and friends who are interested can also refer to it.