Pyridine → 5-(4-Chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (3-methanesulfonyl-phenyl)-amide

HRID 11887

Reaction equation

HRID 11887 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[C:19]([C:21](Cl)=[O:22])[CH:20]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([NH2:34])[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26].N1C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([NH:34][C:21]([C:19]2[CH:20]=[C:10]3[N:9]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH:13]=[C:12]([C:14]([F:16])([F:15])[F:17])[N:11]3[N:18]=2)=[O:22])[CH:31]=[CH:32][CH:33]=1)(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 4280293-(Methylsulphonyl)anilineHCID 70159245-(4-Chlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carbonyl chloride

Product 1

HCID 671326845-(4-Chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (3-methanesulfonyl-phenyl)-amideYield 93.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carbonyl chloride (0.100 g, 0.277 mmol) (prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid using standard procedures, e.g.; thionyl chloride) was added to a solution of 3-methanesulfonyl-phenylamine (0.052 mL, 0.304 mmol) in acetonitrile (10 mL) containing pyridine (0.067 mL, 0.831 mmol). The reaction mixture was stirred overnight at room temperature, diluted with ethyl acetate (25 mL) and washed with 1M hydrochloric acid (50 mL). The organic layer was collected, concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (3-methanesulfonyl-phenyl)-amide (0.128 g, 93%).

Workup

  1. washwashed with 1M hydrochloric acid (50 mL)
  2. customThe organic layer was collected
  3. concentrationconcentrated under reduced pressure
  4. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-99d47705097443a5986f2a6fdfb02356
Source dataset
uspto-grants-2006_08
Patent number
US07098335B2

Linked notes

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