Trifluoroacetic acid → 4-[4-chloro-5-fluoro-2-(1H-pyrazol-4-yl)phenoxy]-3-cyano-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 1401919ノート

反応式

HRID 1401919 の反応式
[Cl:1][C:2]1[C:3]([F:49])=[CH:4][C:5]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([N:30](CC3C=CC(OC)=CC=3OC)[C:31]3[S:35][N:34]=[CH:33][N:32]=3)(=[O:29])=[O:28])=[CH:23][C:22]=2[C:47]#[N:48])=[C:6]([C:8]2[CH:9]=[N:10][N:11](C(OC(C)(C)C)=O)[CH:12]=2)[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([F:49])=[CH:4][C:5]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:31]3[S:35][N:34]=[CH:33][N:32]=3)(=[O:28])=[O:29])=[CH:23][C:22]=2[C:47]#[N:48])=[C:6]([C:8]2[CH:12]=[N:11][NH:10][CH:9]=2)[CH:7]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 59436596tert-butyl 4-[5-chloro-2-(2-cyano-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)-4-fluorophenyl]-1H-pyrazole-1-carboxylate

生成物 1

HCID 468412184-[4-chloro-5-fluoro-2-(1H-pyrazol-4-yl)phenoxy]-3-cyano-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-[5-chloro-2-(2-cyano-4-{[(2,4-dimethoxybenzyl)(1,2,4-thiadiazol-5-yl)amino]sulfonyl}phenoxy)-4-fluorophenyl]-1H-pyrazole-1-carboxylate (Preparation 728, 190 mg, 0.26 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.3 mL, 3.65 mmol) and the reaction mixture was left to stir at room temperature for 16 hours. The reaction was quenched by addition of water (10 mL) and the resulting mixture left to stir for 20 minutes. Then the layers were separated, the organic phase was washed with saturated aqueous sodium chloride solution (5 mL), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The crude oil was purified using ISCO™ (5 g cartridge) 1-20% v/v gradient of methanol in dichloromethane as the eluent. The title compound was obtained as a white solid (61 mg. 50%).

後処理

  1. waitthe reaction mixture was left
  2. customThe reaction was quenched by addition of water (10 mL)
  3. waitthe resulting mixture left
  4. stirringto stir for 20 minutes
  5. customThen the layers were separated
  6. washthe organic phase was washed with saturated aqueous sodium chloride solution (5 mL)
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude oil was purified

出典と根拠

ORDレコード
ord-cf1775d34226445fa0c801d56879eeb0
出典データセット
uspto-grants-2014_12
特許番号
US08907101B2

反応ノート

読み込み中…