Trifluoroacetic acid → N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)-1-phenyl methane sulfonamide

HRID 1038428노트

반응식

HRID 1038428 반응식
[C:1]1([CH2:7][S:8]([NH:11][C:12]2[CH:13]=[C:14]([NH:18][C:19]3[O:20][C:21]([C:24]4[N:25](C(OC(C)(C)C)=O)[C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:22][N:23]=3)[CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[C:24]1[C:21]1[O:20][C:19]([NH:18][C:14]2[CH:13]=[C:12]([NH:11][S:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:10])[CH:17]=[CH:16][CH:15]=2)=[N:23][CH:22]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71060369tert-butyl 2-(2-((3-(phenylmethylsulfonamido)phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate

생성물 1

HCID 71060426N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)-1-phenyl methane sulfonamide수율 71.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of tert-butyl 2-(2-((3-(phenylmethylsulfonamido) phenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 28 (0.24 g, 0.441 mmol) in anhydrous CH2Cl2 (20 mL) was added 1:1 mixture of CH2Cl2:Trifluoroacetic acid (10 mL) at room temperature. Reaction was stirred for 1.5 hour at ambient temperature. It was quenched with aq. saturated NaHCO3 and CH2Cl2 layer was separated. After evaporation of solvent, crude product was purified using MPLC silica column (Biotage) (Acetone/hexane as an eluent) to obtain N-(3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenyl)-1-phenyl methane sulfonamide 29 (0.14 g, 71% yield).

후처리

  1. customat room temperature
  2. customReaction
  3. customIt was quenched with aq. saturated NaHCO3 and CH2Cl2 layer
  4. customwas separated
  5. customAfter evaporation of solvent, crude product
  6. customwas purified

출처 및 근거

ORD 기록
ord-66f17183c4cc47d1a0f06158e4eb687b
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551992B2

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