Ammonia → HCID 56646141, compound

HRID 1773598Notes

Reaction equation

HRID 1773598 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]3[CH:21]=[CH:20][CH:19]=[N:18][C:17]=23)=[O:12])=[C:6]([O:22][CH3:23])[CH:5]=1.[OH-].[NH4+:26].N>C(#N)C.CS(C)=O>[C:3]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]3[CH:21]=[CH:20][CH:19]=[N:18][C:17]=23)=[O:12])=[C:6]([O:22][CH3:23])[CH:5]=1)(=[O:2])[NH2:26]

Participants

6

Reactant 3

HCID 222Ammonia3×HCID 14923Ammonium Hydroxide3×HCID 58056377HCID 58056377, compound3×

Product 1

HCID 56646141HCID 56646141, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 3-methoxy-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-benzoic acid methyl ester (5 mg) and an aqueous solution of ammonium hydroxide (concentrated, 1 mL) and a mixture of 3-methoxy-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-benzoic acid methyl ester (5 mg) and a solution of ammonia (2 M in MeOH, 1 mL) were stirred at room temperature for 2 days. The two mixtures were then combined and dimethyl sulfoxide (1 mL) was added followed by acetonitrile (1 mL). A solution of ammonia (2 M in MeOH, 1 mL) and an aqueous solution of ammonium hydroxide (concentrated, 2 mL) were then added and the resulting mixture was heated to 50° C. for 24 hours. A second portion of 3-methoxy-4-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-benzoic acid methyl ester (35 mg) was added followed by dimethyl sulfoxide (5 mL), acetonitrile (5 mL), a solution of ammonia (2 M in MeOH, 5 mL) and an aqueous solution of ammonium hydroxide (concentrated, 5 mL) and the resulting mixture was heated to 85° C. for 3 days. The white precipitate which formed was collected by filtration, washed with water, methanol and diethyl ether to afford after drying 15 mg (35% yield) of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (4-carbamoyl-2-methoxy-phenyl)-amide as light yellow solid. MS=312 [M+H]+.

Workup

  1. customThe white precipitate which formed
  2. filtrationwas collected by filtration
  3. washwashed with water, methanol and diethyl ether
  4. customto afford

Sources & evidence

ORD record
ord-ae14de68c0184419aa93fa67b2257fb0
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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