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Hydrochloric Acid → methyl 1-(3-chloropyridin-2-yl)-3-{[4-(trifluoromethyl)phenyl]carbamoyl}-1H-pyrazole-5-carboxylate

HRID 1630673
ノート
印刷プレビュー

反応式

HRID 1630673 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([C:17]([OH:19])=O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:20][C:21]([F:30])([F:29])[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.Cl>ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([C:17](=[O:19])[NH:26][C:25]3[CH:27]=[CH:28][C:22]([C:21]([F:20])([F:29])[F:30])=[CH:23][CH:24]=3)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 665876291-(3-chloropyridin-2-yl)-5-(methoxycarbonyl)-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 66587470methyl 1-(3-chloropyridin-2-yl)-3-{[4-(trifluoromethyl)phenyl]carbamoyl}-1H-pyrazole-5-carboxylate

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒3 回

反応条件

温度
20 °C

実験手順

A solution of 1.00 g (3.55 mmol) of 1-(3-chloropyridin-2-yl)-5-(methoxycarbonyl)-1H-pyrazole-3-carboxylic acid in 13 ml of dichloromethane and 1.3 ml of N,N-dimethylformamide was cooled to 0° C., a solution of 0.86 g (5.33 mmol) of 4-(trifluoromethyl)aniline in 3 ml of dichloromethane was added dropwise and 0.68 g (3.55 mmol) of N-ethyl-N′-3-(dimethylaminopropyl)carbodiimide×HCl and 87 mg (710 μmol) of 4-dimethylaminopyridine were added a little at a time. The mixture was stirred at 0° C. for 2 hours and at 20° C. for 16 hours. The mixture was then diluted with dichloromethane and washed successively with 1 N aqueous hydrochloric acid and water. The organic phase was dried over sodium sulphate, the solvent was removed under reduced pressure and the residue was purified on silica gel using cyclohexane/ethyl acetate=3:1→2:1. (logP: 3.54).

後処理

  1. washwashed successively with 1 N aqueous hydrochloric acid and water
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified on silica gel

出典と根拠

ORDレコード
ord-e73accd471de4780bf737e466f3db354
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08791139B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート