Ammonia → 5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [2-(3-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-amide

HRID 474368Notes

Reaction equation

HRID 474368 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][C:14]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[N:17]=[CH:16][CH:15]=3)=[O:12])=[C:4]2[N:3]=1.[NH3:29]>C(O)C>[F:26][C:25]([F:28])([F:27])[C:21]1[CH:20]=[C:19]([N:18]2[C:14]([NH:13][C:11]([C:10]3[CH:9]=[N:8][N:5]4[CH:6]=[CH:7][C:2]([NH2:29])=[N:3][C:4]=34)=[O:12])=[CH:15][CH:16]=[N:17]2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 580631105-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 580630815-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [2-(3-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-amideYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (210 mg, 0.52 mmol) in ethanol (20 mL) saturated with ammonia was heated to 100° C. overnight in a sealed tube. After cooling to room temperature, solvent was removed under reduced pressure, and the resultant residue was purified by preparative HPLC to afford 5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [2-(3-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-amide (8 mg, yield: 4%). 1H NMR (DMSO, 400 MHz): δ 9.94 (s, 1H), 8.62 (d, J=7.6 Hz, 1H), 8.16 (s, 1H), 7.49-7.69 (m, 8H), 6.53 (s, 1H), 6.37 (d, J=7.6 Hz, 1H). MS (ESI) m/z: 388.1

Workup

  1. customsolvent was removed under reduced pressure
  2. customthe resultant residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0ed183a439c14c789e5e80aed9ac210a
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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