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

HRID 1692215노트

반응식

HRID 1692215 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-2ddf453ae2734ff6ab6257cd1c176fb2
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153814B2

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