Diisopropylethylamine → 5-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 474367Notes

Reaction equation

HRID 474367 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([NH2:14])=[CH:12][CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[Cl:17][C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([C:27](Cl)=[O:28])=[C:20]2[N:19]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:17][C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([C:27]([NH:14][C:13]3[N:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=4)[N:10]=[CH:11][CH:12]=3)=[O:28])=[C:20]2[N:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 433167702-(3-Trifluoromethylphenyl)-2H-pyrazol-3-ylamineHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride

Product 1

HCID 580631105-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine (200 mg, 0.88 mmol) in dichloromethane (30 mL) was added 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (215 mg, 1.0 mmol) and diisopropylethylamine (130 mg, 1.0 mmol). The mixture was heated to 50° C. overnight. After cooling to room temperature, the mixture was concentrated to afford crude 5-chloro-N-(1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (210 mg, yield 58%), which was used for the next step without further purification. MS (ESI) m/z: 407.2

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-af9af61c59c34225bfe8c47e59d73f36
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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