Trifluoroacetic acid → (S)-N-(2-fluorophenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 627040노트

반응식

HRID 627040 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[N:19]([C:20](=[O:39])[C@@H:21]([NH:25][C:26](=[O:38])[C@@H:27]([N:29](C)[C:30](=O)OC(C)(C)C)[CH3:28])[CH:22]([CH3:24])[CH3:23])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12]1)=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[N:19]([C:20](=[O:39])[C@@H:21]([NH:25][C:26](=[O:38])[C@@H:27]([NH:29][CH3:30])[CH3:28])[CH:22]([CH3:23])[CH3:24])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12]1)=[O:10]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 131735262tert-butyl (S)-1-((S)-1-((S)-2-(2-fluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

생성물 1

HCID 73603482(S)-N-(2-fluorophenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide수율 78.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-1-((S)-2-(2-fluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (39 mg, 72.0 μmol, Eq: 1.00) was combined with DCM (3.00 mL) to give a colorless solution. TFA (1.00 mL, 13.0 mmol, Eq: 180) was added the reaction was stirred at rt for 30 min and then concentrated in vacuo. The residue was taken up in DCM, washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give (S)—N-(2-fluorophenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide as an off-white solid (25 mg), m/z=442 (M+H).

후처리

  1. customto give a colorless solution
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-480edb7bc125411b864ffb66fafca22b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309248B2

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