Category: 1152582-56-3

Synthetic Route of 1152582-56-3, 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 1152582-56-3 as follows.

Example 22 N-(5-(4-fluorophenyl)-11-methyl-1-oxo-2,4,5,11-tetrahydro-1H-2,5,6,11-tetraazadibenzo[cd,h]azulen-8-yl)-2-(1-methyl-1H-pyrazol-4-yl)acetamide [0706] A stock solution of Example 14e and N,N-diisopropylethylamine (0.11 M and 0.33 M in N,N-dimethylacetamide, respectively, 350 muL, 0.038 mmol Example 14e and 0.11 mmol N,N-diisopropylethylamine), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.13 M in N,N-dimethylacetamide, 350 muL, 0.046 mmol), and 2-(1-methyl-1H-pyrazol-4-yl)acetic acid (0.40 M in N,N-dimethylacetamide, 113 muL, 0.050 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C., and passed through the reactor at 180 muL per minute (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by reverse phase HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) to yield the title compound as an impure mixture. The material was dissolved in methanol (1 mL) and manually injected into the HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) give 0.0067 g (38%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) delta 8.49 (d, J=2.44 Hz, 1H), 8.45 (d, J=2.75 Hz, 1H), 7.77 (s, 1H), 7.63 (s, 1H), 7.40 (s, 1H), 7.07 (s, 1H), 6.87 (m, 2H), 6.57 (m, 2H), 4.60 (m, 2H), 4.07 (s, 3H), 3.81 (s, 3H), 3.55 (s, 2H). MS (APCI+) m/z 484.1 (M+H)+.

According to the analysis of related databases, 1152582-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Dachun; Pratt, John; Wang, Le; Hasvold, Lisa A.; Bogdan, Andrew; US2014/256710; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1152582-56-3, 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 1152582-56-3 as follows.

Example 22 N-(5-(4-fluorophenyl)-11-methyl-1-oxo-2,4,5,11-tetrahydro-1H-2,5,6,11-tetraazadibenzo[cd,h]azulen-8-yl)-2-(1-methyl-1H-pyrazol-4-yl)acetamide [0706] A stock solution of Example 14e and N,N-diisopropylethylamine (0.11 M and 0.33 M in N,N-dimethylacetamide, respectively, 350 muL, 0.038 mmol Example 14e and 0.11 mmol N,N-diisopropylethylamine), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.13 M in N,N-dimethylacetamide, 350 muL, 0.046 mmol), and 2-(1-methyl-1H-pyrazol-4-yl)acetic acid (0.40 M in N,N-dimethylacetamide, 113 muL, 0.050 mmol) were aspirated from their respective source vials, mixed through a perfluoroalkoxy mixing tube (0.2 mm inner diameter), and loaded into an injection loop. The reaction segment was injected into the flow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mL internal volume) set at 100 C., and passed through the reactor at 180 muL per minute (10 minute residence time). Upon exiting the reactor, the reaction mixture was loaded directly into an injection loop and purified by reverse phase HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) to yield the title compound as an impure mixture. The material was dissolved in methanol (1 mL) and manually injected into the HPLC(C8, acetonitrile/water (0.1% ammonium acetate), 5-100%) give 0.0067 g (38%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) delta 8.49 (d, J=2.44 Hz, 1H), 8.45 (d, J=2.75 Hz, 1H), 7.77 (s, 1H), 7.63 (s, 1H), 7.40 (s, 1H), 7.07 (s, 1H), 6.87 (m, 2H), 6.57 (m, 2H), 4.60 (m, 2H), 4.07 (s, 3H), 3.81 (s, 3H), 3.55 (s, 2H). MS (APCI+) m/z 484.1 (M+H)+.

According to the analysis of related databases, 1152582-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Dachun; Pratt, John; Wang, Le; Hasvold, Lisa A.; Bogdan, Andrew; US2014/256710; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1152582-56-3, 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. 1152582-56-3 name is 2-(1-Methyl-1H-pyrazol-4-yl)acetic 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.

(Step 4) A solution of 2-amino-2-(4-(methoxymethyl)phenyl)-N-(4-(trimethylsilyl)phenyl)acetamide (104 mg, 0.30 mmol), 2-(1-methyl-1H-pyrazol-4-yl)acetic acid (51.1 mg, 0.36 mmol), HATU (150 mg, 0.39 mmol) and DIEA (0.106 mL, 0.61 mmol) in DMF (1.5 mL) was stirred at room temperature for 10 hr. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 40?80% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (45.0 mg, 0.097 mmol, 31.9%) as white crystals. MS(API): Calculated 464.6, Found 465.1(M+H) 1H NMR(300 MHz,DMSO-d6):delta0.17-0.22(9H,m),3.31(3H,s),3.38(2H,s),3.76(3H,s),4.37(2H,s),5.63(1H ,d,J=7.9 Hz),7.24-7.34(3H,m),7.39-7.60(7H,m),8.71(1H,d,J=7. 9 Hz),10.35(1H,s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1-Methyl-1H-pyrazol-4-yl)acetic acid, and friends who are interested can also refer to it.

Reference of 1152582-56-3, These common heterocyclic compound, 1152582-56-3, name is 2-(1-Methyl-1H-pyrazol-4-yl)acetic 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 suspension of 6-(3-methylimidazol-4-yl)isoquinolin-3-amine (XLVIII) (100 mg, 0.45 mmol), 2-(1-methylpyrazol-4-yl)acetic acid (XLIX (purchased from Enamine) (75 mg, 0.54 mmol), DMAP (27.2 mg, 0.22 mmol) and HATU (203.5 mg, 0.54 mmol) in DMF (5 mL) was added DIPEA (0.19 mL, 1.1 mmol). The resulting mixture was stirred at 80 C. for 1.5 h. The reaction mixture was cooled to room temperature and poured into water. The resulting solid was filtered and purified by silica gel chromatography (0?10% MeOH/CHCl3). The fractions containing the product were concentrated. The product was further purified by HPLC (0?35% MeCN/water) and the fractions containing the product concentrated, re-dissolved in MeOH and filtered through bicarbonate resin. The filtrate was concentrated and triturated in ether, filtered and dried under high vacuo to afford N-(6-(1-methyl-1H-imidazol-5-yl)isoquinolin-3-yl)-2-(1-methyl-1H-pyrazol-4-yl)acetamide 47 as a white solid (20.0 mg, 0.058 mmol, 12.9% yield). 1H NMR (499 MHz, DMSO-d6) delta ppm 3.59 (2H, s), 3.79 (3H, s), 3.82 (3H, s), 7.30 (1H, d, J=0.82 Hz), 7.36 (1H, s), 7.61 (1H, s), 7.67 (1H, dd, J=8.51, 1.65 Hz), 7.79 (1H, s), 7.99 (1H, s), 8.09 (1H, d, J=8.51 Hz), 8.50 (1H, s), 9.13 (1H, s), 10.66 (1H, s); ESIMS found for C19H18N6O m/z 347.2 (M+1).

The synthetic route of 1152582-56-3 has been constantly updated, and we look forward to future research findings.