923283-54-9|Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate| Ambeed

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Quality Control of [ 923283-54-9 ] Purity: 98% SDS Specification

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Product Details of [ 923283-54-9 ]

CAS No. :	923283-54-9
Formula :	C₆H₉N₃O₂
M.W :	155.16
SMILES Code :	O=C(C1=C(N)C=NN1C)OC
MDL No. :	MFCD04969992
InChI Key :	WMYQZQLKVASMIV-UHFFFAOYSA-N
Pubchem ID :	4715109

Safety of [ 923283-54-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	1759
Packing Group:	Ⅲ

Application In Synthesis of [ 923283-54-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 923283-54-9 ]

[ 923283-54-9 ] Synthesis Path-Downstream 1~35

1
[ 923283-54-9 ]
[ 3473-63-0 ]
[ 314021-93-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 110℃; for 1h;	Compound 8: To a solution of 7 (0.92 g, 5.9 mmol) in 5 mL of Hunig's base and 5 mL of n-butanol was added formamidine acetate (0.68 g, 6.5 mmol). The reaction mixture was heated and stirred at 110 C. for 1 hour. After cooling to room temperature, the white precipitate was collected by filtration and washed with diethyl ether. The resulting white precipitate was dried under reduced pressure to afford 8 (0.83 g, 94%). 1H NMR (d6-DMSO) δ 4.33 (s, 3H) 8.50 (s, 1H) 8.80 (s, 1H); ES (+) MS m/e=151 (M+1).

References: [1]Patent: US2007/27166,2007,A1 .Location in patent: Page/Page column 80.

2
[ 309740-49-6 ]
[ 923283-54-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 16h;	Methyl 1 -methyl-4-nitro-1 H-pyrazole-5-carboxylate (10 g, 51.31 mmol, 1. eq.) and palladium carbon (11.50 g, 103 mmol, 2.00 eq) was suspended in methanol (100 ml_). The resulting solution was stirred under hh atmosphere for 16 h at 25 C. The solids were filtered. The resulting mixture was concentrated under vacuum. The residue was purified by column chromatography (Method A). Methyl 4-amino-i -methyl-i H-pyrazole-5-carboxylate was isolated as a pink solid, (9 g, quant); LCIMS (Method J): Rt 0.64i mi [MH]+ i56.i mlz.
97%	With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 2h;	General procedure: To a solution of 15a (3.57 g, 16.8 mmol) in MeOH (60 mL) wasadded Pd/C (50% wet, 0.178 g), and the mixture was stirred at room temperature for 2 h under hydrogen atmosphere. The insolublematerials were filtered off by using a pad of Celite, and the Celitewas washed with MeOH. The filtrate was concentrated in vacuo.The residue was diluted with EtOAc, washed with brine, dried overMgSO4, and filtered. The filtrate was concentrated in vacuo toafford 16a
95.2%	With palladium on activated charcoal; hydrogen; In methanol; at 25℃; for 3h;	1-methyl-4-nitro-1H-pyrazole-5-carboxylate(1.0 g, 5.4 mmol) was dissolved in methanol (30 mL)Palladium on carbon (100 mg),Access to hydrogen,25 C for 3 hours,filter,The filtrate was concentrated in vacuo to give the product(0.8 g, yield: 95.2%).

91%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 3h;	Compound 7: 10% wt. Pd/C (0.15 g, 0.14 mmol) was added to a solution containing 6 (0.26 g, 1.4 mmol) in 10 mL of methanol. The mixture was stirred under a hydrogen atmosphere at ambient temperature. After 3 hours, the reaction mixture was filtered thru a plug of Celite. The resulting filtrate was concentrated under reduced pressure to afford 7 (0.20 g, 91%), ES (+) MS m/e=156 (M+1).
90%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 1551.49 Torr; for 5h;	Methyl 2-methyl-4-nitro-2H-pyrazole-3-carboxylate (4.00 g, 21.6 mmol) was dissolved in methanol (120 mL), dry palladium on carbon (10% palladium, 1% water, 400 mg) was added. The reaction solution was allowed to react under 30 psi hydrogen pressure for 5 hours at room temperature. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure to give methyl 4-amino-2-methyl-2H-pyrazole-3-carboxylate (3.00 g, as an off-white solid) with a yield of 90%. 1H NMR: (400 MHz, CDCl3) δ 7.10(s, 1H), 4.09(s, 2H), 4.02(s, 3H), 3.90(s, 3H). MS-ESI calcd. [M + H]+ 156, found 156.
41%	With hydrogen;palladium 10% on activated carbon; In methanol; under 30402.0 Torr; for 2h;	127 mg (0.69 mM) of the compound obtained in Preparative Example 13 was dissolved in 3 ml of methanol, to which 10% palladium/charcoal was added, and the resulting mixture was stirred under hydrogen pressure of 40 atm for 2 hours. After the reaction was terminated, the resulting reaction solution was filtered through cellite, and distilled under reduced pressure, to obtain 43 mg (41%) of the title compound.1H NMR (300 MHz, CDCl3) δ 3.92 (s, 3H), 4.04 (s, 3H), 4.09 (br, NH2), 7.08 (s, 1H).Mass: 155 (M+)
41%	With hydrogen;palladium 10% on activated carbon; In methanol; under 30402.0 Torr; for 2h;	127 mg (0.69 mM) of the compound obtained in Preparative Example 13 was dissolved in 3 ml of methanol, to which 10% palladium/charcoal was added, and the resulting mixture was stirred under hydrogen pressure of 40 arm for 2 hours. After the reaction was terminated, the resulting reaction solution was filtered through cellite, and distilled under reduced pressure, to obtain 43 mg (41%) of the title compound.1H NMR(300MHz, CDCl3) δ 3.92(s, 3H), 4.04(s, 3H), 4.09(br, NH2), 7.08(s, IH). Mass : 155(M+)
	With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; at 20℃; for 6h;	[0228] To a solution of methyl l-methyl-4-nitro-lH-pyrazole-5-carboxylate (1.5 g) in THF (20 mL) was added Pd/C (500 mg, 10%). The solution was stirred under a hydrogen atmosphere for 6 h at RT. The reaction mixture was filtered, dried over sodium sulfate, filtered, and concentrated to give 1.1 g of crude methyl 4-amino-l- methyl-lH-pyrazole-5-carboxylate. LCMS: 156 (M+H) +.
4.71 g	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2068.65 Torr; for 4h;	B) Methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate To a solution of methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate (8.62 g) in methanol (100 mL), palladium-carbon (10%) (0.86 g) was added, and the mixture was stirred at room temperature for 4 hours in a hydrogen atmosphere (40 psi). Palladium-carbon was filtered off, and then, the filtrate was concentrated to obtain the title compound (4.71 g). 1H NMR (400 MHz, CDCl3) δ 3.91 (3H, s), 4.03 (3H, s), 4.15 (2H, brs), 7.07 (1H, s).

References: [1]Patent: WO2020/49017,2020,A1 .Location in patent: Page/Page column 56-57.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2452 - 2465.
[3]Patent: CN107226807,2017,A .Location in patent: Paragraph 0277-0279.
[4]Patent: US2007/27166,2007,A1 .Location in patent: Page/Page column 80-81.
[5]Journal of Medicinal Chemistry,2020,vol. 63,p. 7369 - 7391.
[6]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0449; 0450; 0451.
[7]Bioorganic and Medicinal Chemistry Letters,2021,vol. 41.
[8]Patent: US2010/63106,2010,A1 .Location in patent: Page/Page column 12.
[9]Patent: WO2008/51047,2008,A1 .Location in patent: Page/Page column 29.
[10]Patent: WO2009/26241,2009,A1 .Location in patent: Page/Page column 67.
[11]Tetrahedron Letters,2009,vol. 50,p. 2624 - 2627.
[12]Patent: EP3287441,2018,A1 .Location in patent: Paragraph 0306.

3
[ 923283-54-9 ]
[ 598-21-0 ]
[ 1021498-14-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In tetrahydrofuran;Inert atmosphere;	Preparative Example 15 4-(2-bromoacetylamino)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester 42 mg (0.27 mM) of the compound obtained in Preparative Example 14 was dissolved in 1 ml of tetrahydrofuran, to which 28 μl (0.32 mM) of bromo acetylbromide and 57 μl (0.41 mM) of triethylamine were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 1 hours. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 36 mg (85%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 4.03 (s, 3H), 4.11 (s, 3H), 4.05 (s, 2H), 8.37 (s, 1H), 10.01 (br, NH).
85%	With triethylamine; In tetrahydrofuran; for 1h;	42 mg (0.27 mM) of the compound obtained in Preparative Example 14 was dissolved in 1 ml of tetrahydrofuran, to which 28 μl (0.32 mM) of bromo acetylbromide and 57 μl (0.41 mM) of triethylamine were added EPO <DP n="32"/>dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 1 hours. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane : ethyl acetate = 2 : 1), to obtain 36 mg(85%) of the title compound.1H NMR(300MHz, CDCl3) δ 4.03(s, 3H), 4.1 l(s, 3H), 4.05(s, 2H), 8.37(s, IH), 10.01(br, NH).

References: [1]Patent: US2010/63106,2010,A1 .Location in patent: Page/Page column 12.
[2]Patent: WO2008/51047,2008,A1 .Location in patent: Page/Page column 29-30.

4
[ 923283-54-9 ]
[ 403-43-0 ]
[ 1123784-03-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In tetrahydrofuran; at 20℃; for 4h;	[0229] To a solution of methyl 4-amino-l -methyl- lH-pyrazole-5-carboxylate (1 g) in THF (20 mL) was added TEA (1.2 mL) and 4-fluorobenzoyl chloride (1.3 g). After 4 h at RT, the mixture was concentrated to residue, taken up in ethyl acetate (50 mL) washed with sodium bicarbonate solution (50 mL), and washed with NaCl solution (50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (20% ethyl acetate/petroleum ether) gave methyl 4-(4-fluorobenzamido)-l-methyl-lH-pyrazole-5-carboxylate (0.8 g, 45%). LCMS: 278 (M+H) +.

References: [1]Patent: WO2009/26241,2009,A1 .Location in patent: Page/Page column 67-68.

5
[ 923283-54-9 ]
methyl 4-((4-(3-cyano-4-(((3R,4S)-3-fluoropiperidin-4-yl)oxy)phenyl)-1,3,5-triazin-2-yl)amino)-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]

References: [1]Patent: US2016/96827,2016,A1 .

6
[ 923283-54-9 ]
2-(((3R,4S)-3-fluoropiperidin-4-yl)oxy)-5-(4-((5-(hydroxymethyl)-1-methyl-1H-pyrazol-4-yl)amino)-1,3,5-triazin-2-yl)benzonitrile [ No CAS ]

References: [1]Patent: US2016/96827,2016,A1 .

7
[ 923283-54-9 ]
2-(((3R,4S)-3-fluoro-1-((S)-2-hydroxypropanoyl)piperidin-4-yl)oxy)-5-(4-((5-(hydroxymethyl)-1-methyl-1H-pyrazol-4-yl)amino)-1,3,5-triazin-2-yl)benzonitrile [ No CAS ]

References: [1]Patent: US2016/96827,2016,A1 .

8
[ 923283-54-9 ]
(3R,4S)-tert-butyl 4-(2-cyano-4-(4-((5-(methoxycarbonyl)-1-methyl-1H-pyrazol-4-yl)amino)-1,3,5-triazin-2-yl)phenoxy)-3-fluoropiperidine-1-carboxylate [ No CAS ]

References: [1]Patent: US2016/96827,2016,A1 .

9
[ 2831-66-5 ]
[ 923283-54-9 ]
methyl 4-((4-chloro-1,3,5-triazin-2-yl)amino)-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 0.5h;	To a solution of 2,4-dichloro-1,3,5-triazine (665 mg, 4.43 mmol) in dichloromethane (30 mL) at 0 C., <strong>[923283-54-9]methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate</strong> (0.62 g, 4 mmol) in dichloromethane (5 mL+5 mL wash) was added, followed by N,N-Diisopropylethylamine (1.05 mL, 6 mmol). The reaction mixture was stirred at 0 C. for 30 minutes. After this time, the reaction was quenched with saturated sodium bicarbonate solution (PH˜8) and extracted with dichloromethane for three times. The combined extracts were washed once with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel) to give the desired product as white solid. LCMS-ESI+ (m/z): [M+H]+ calcd for C9H10ClN6O2: 269.7. found: 269.1.

References: [1]Patent: US2016/96827,2016,A1 .Location in patent: Paragraph 1836.

10
[ 923283-54-9 ]
(1R,2R)-2-(4-bromobenzoyl)cyclohexane-1-carboxylic acid [ No CAS ]
methyl 4-([(1R,2R)-2-(4-bromobenzoyl)cyclohexyl]carbonyl}amino)-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; at 73 - 77℃; for 2h;	Intermediate 45: Methyl 4-([(lR,2R)-2-(4-bromobenzoyl)cyclohexyl]carbonyl}- amino)-l-methyl-lH-pyrazole-5-carboxylate Et3N (1.8 mL, 12.99 mmol) and T3P (50% in EtOAc, 4 mL, 6.72 mmol) were added to a solution of (li?,2i?)-2-(4-bromobenzoyl)cyclohexanecarboxylic acid (1 g, 3.21 mmol) and methyl 4-amino-l -methyl- lH-pyrazole-5-carboxylate (1 g, 6.45 mmol) in EtOAc (15 mL) and the reaction mixture was stirred at rt for lh and then heated at 73-77C for 2h. The reaction mixture was diluted with EtOAc (100 mL) and the organic phase was washed with NaHC03 (sat, aq), dried using a phase separator and concentrated in vacuum. The residue was purified by flash chromatography (30%→100% EtOAc in heptane) to give the title compound (1.22 g, 85%) as a white solid. NMR (500 MHz, CDC1 ) δ 1.25 - 1.40 (m, 1H), 1.43 (dqt, 2H), 1.71 (qd, 1H), 1.84 - 1.95 (m, 2H), 1.99 - 2.08 (m, 1H), 2.11 (dd, 1H), 2.92 (ddd, 1H), 3.67 (ddd, 1H), 4.03 (s, 3H), 4.07 (s, 3H), 7.56 - 7.63 (m, 2H), 7.8 - 7.87 (m, 2H), 8.12 (s, 1H), 8.88 (s, 1H). MS m/z 448 [M+H]+

References: [1]Patent: WO2016/177703,2016,A1 .Location in patent: Page/Page column 69-70.
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 4312 - 4324.

11
[ 923283-54-9 ]
N,1-dimethyl-4-[({(1R,2R)-2-[4-(5-methyl-1H-pyrazol-3-yl)benzoyl]cyclohexyl}carbonyl)amino]-1H-pyrazole-5-carboxamide [ No CAS ]

References: [1]Patent: WO2016/177703,2016,A1 .

12
[ 923283-54-9 ]
methyl 1-methyl-4-([(1R,2R)-2-{4-[3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]benzoyl}cyclohexyl]carbonyl}amino)-1H-pyrazole-5-carboxylate [ No CAS ]

References: [1]Patent: WO2016/177703,2016,A1 .
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 4312 - 4324.

13
[ 923283-54-9 ]
N,1-dimethyl-4-([(1R,2R)-2-{4-[3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]benzoyl}cyclohexyl]carbonyl}amino)-1H-pyrazole-5-carboxamide [ No CAS ]

References: [1]Patent: WO2016/177703,2016,A1 .

14
[ 923283-54-9 ]
1-methyl-4-([(1R,2R)-2-{4-[3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]benzoyl}cyclohexyl]carbonyl}amino)-1H-pyrazole-5-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/177703,2016,A1 .
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 4312 - 4324.

15
[ 923283-54-9 ]
[ 3473-63-0 ]
1-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 110℃; for 1h;	A mixture of methyl 4-amino-i-methyl-1H-pyrazole-5-carboxylate (0.40 g, 2.1 mmol), formimidamide acetic acid salt (0.24 g, 2.3 mmol) and diisopropylethylamine (1.82 ml,10.5 mmol) in n-butanol (2 mL) was stirred at 110 C. After 1 h at 110 C and subsequent cooling to room temperature, a precipitate had formed. The precipitate was collected by filtration, was washed with diethyl ether and dried at 35 C in vacuo to give0.31 g (1.96 mmol, 94% yield) of the title compound as a white solid. Purity 98%. 1H NMR (400 MHz, DMSO-d6) ö ppm 7.94 (s, 1H), 7.83 (s, 1H), 4.16 (s, 3H).UPLC/MS (3 mm) retention time 0.57 mm.LRMS: mlz 151 (M+1).

References: [1]Patent: WO2017/64068,2017,A1 .Location in patent: Page/Page column 33; 34.

16
[ 138786-86-4 ]
[ 923283-54-9 ]

References: [1]Patent: CN107226807,2017,A .
[2]Patent: WO2008/51047,2008,A1 .
[3]Journal of Medicinal Chemistry,2020,vol. 63,p. 7369 - 7391.

17
[ 923283-54-9 ]
[ 107-14-2 ]
methyl 4-((1-amino-2-chloroethylidene)amino)-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.7%	With hydrogenchloride; In 1,4-dioxane; at 25℃; for 3h;	4-amino-1-methyl-1H-pyrazole-5-carboxylate(0.8 g, 5.2 mmol) and 2-chloroacetonitrile(0.8 g, 10.6 mmol)Dissolved in hydrogen chloride in a 1,4-dioxane solution (4 mol / L, 12 mL)25 C for 3 hours.The reaction solution was concentrated in vacuo,Ethyl acetate (30 mL) was added,The product was filtered (0.8 g, yield: 66.7%).

References: [1]Patent: CN107226807,2017,A .Location in patent: Paragraph 0280-0282.

18
[ 923283-54-9 ]
N-(cyclopropylmethyl)-2-(4-(4-methoxybenzoyl) piperidin-1-yl)-N-((1-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)methyl)acetamide [ No CAS ]

References: [1]Patent: CN107226807,2017,A .

19
[ 923283-54-9 ]
2-chloro-N-(cyclopropylmethyl)-N-((1-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)methyl)acetamide [ No CAS ]

References: [1]Patent: CN107226807,2017,A .

20
[ 923283-54-9 ]
2-(4-(4-cyanophenoxy)piperidin-1-yl)-N-(cyclopropylmethyl)-N-((1-methyl-7-oxo-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)methyl)acetamide [ No CAS ]

References: [1]Patent: CN107226807,2017,A .

21
[ 923283-54-9 ]
5-(chloromethyl)-1-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one [ No CAS ]

References: [1]Patent: CN107226807,2017,A .

22
[ 923283-54-9 ]
5-(((cyclopropylmethyl)amino)methyl)-1-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one [ No CAS ]

References: [1]Patent: CN107226807,2017,A .

23
[ 923283-54-9 ]
methyl 2-methyl-4-[methyl-(2,2,2-trifluoroacetyl)amino]-2H-pyrazole-3-carboxylate [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

24
[ 923283-54-9 ]
4-(tert-butoxycarbonylmethylamino)-2-methyl-2H-pyrazole-3-carboxylic acid [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

25
[ 923283-54-9 ]
tert-butyl (5-carbamoyl-1-methyl-1H-pyrazol-4-yl)methylcarbamate [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

26
[ 923283-54-9 ]
[ 292638-85-8 ]
methyl 4-[(3-methoxy-3-oxopropyl)amino]-1-methyl-1H-pyrazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.25 g	With acetic acid; at 165℃; for 1h;Microwave irradiation;	C) Methyl 4-[(3-methoxy-3-oxopropyl)amino]-1-methyl-1H-pyrazole-5-carboxylate To a mixture of <strong>[923283-54-9]methyl 4-amino-1-methyl-1H-pyrazole-5-carboxylate</strong> (4.71 g) and methyl acrylate (3.14 g), acetic acid (0.4 g) was added, and the resulting mixture was stirred at 165C for 1 hour under irradiation with microwave. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to obtain the title compound (2.25 g). 1H NMR (400 MHz, CDCl3) δ 2.61 (2H, t J = 6.4 Hz), 3.38-3.46 (2H, m), 3.70 (3H, s), 3.89 (3H, s), 4.03 (3H, s), 5.04 (1H, brs), 7.06 (1H, s).
	With dmap; In N,N-dimethyl-formamide; at 100℃; for 72h;	General procedure: A mixture of 16a (2.92 g, 15.9 mmol), methyl acrylate (13.7 g,159 mmol), and DMAP (0.389 g, 3.19 mmol) in DMF (20 mL) wasstirred at 100 C for 3 days. The resulting mixture was cooled toroom temperature, and the excess methyl acrylate was removedin vacuo. To the residue were added benzyl bromide (2.84 mL,23.9 mmol) and K2CO3 (3.30 g, 23.9 mmol). The mixture was stirredat room temperature for 8 h. The mixture was diluted withwater (200 mL) and extracted with EtOAc (200 mL). The organiclayer was washed with brine, dried over MgSO4, and filtered. Thefiltrate was concentrated in vacuo, and the residue was purifiedby column chromatography (silica gel, eluted with 0-20% EtOAcin hexane) to give 18a

References: [1]Patent: EP3287441,2018,A1 .Location in patent: Paragraph 0307.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2452 - 2465.

27
[ 923283-54-9 ]
2-chloro-N-(3-chloro-4-(3,4-dimethoxybenzoyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridin-7-yl)benzamide [ No CAS ]