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

HRID 11887

反応式

HRID 11887 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-99d47705097443a5986f2a6fdfb02356
出典データセット
uspto-grants-2006_08
特許番号
US07098335B2

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