(R)-3-Pyrrolidinol → 5-[(e)-3-Chloro-2-(1-chloro-vinyl)-penta-2,4-diene-1-sulfonyl]-3-[-1-{4-[3-((r)-3-hydroxy-pyrrolidin-1-yl)-3-oxo-propyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359885노트

반응식

HRID 1359885 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][CH2:31][C:32]([OH:34])=O)[C:25]=1[CH3:35])(=[O:12])=[O:11].[NH:36]1[CH2:40][CH2:39][C@@H:38]([OH:41])[CH2:37]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1]/[C:2](/[CH:7]=[CH2:6])=[C:3](/[C:4]([Cl:8])=[CH2:5])\[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][CH2:31][C:32]([N:36]2[CH2:40][CH2:39][C@@H:38]([OH:41])[CH2:37]2)=[O:34])[C:25]=1[CH3:35])(=[O:12])=[O:11]

참가 물질

5

반응물 3

HCID 2759337(R)-3-PyrrolidinolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 590776223-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic Acid

생성물 1

HCID 870711015-[(e)-3-Chloro-2-(1-chloro-vinyl)-penta-2,4-diene-1-sulfonyl]-3-[-1-{4-[3-((r)-3-hydroxy-pyrrolidin-1-yl)-3-oxo-propyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic acid (267 mg), (R)-pyrrolidin-3-ol (2 eq.), HATU (1.2 eq.) and TEA (0.2 mL) in DMF (2 mL) was stirred at rt for 2 hours. The reaction was concentrated, diluted with DCM, washed with water (2×), sodium carbonate (2×), dried and concentrated. The residue was purified on a silica gel column to give 16 mg of the titled compound as a yellow solid.

후처리

  1. concentrationThe reaction was concentrated
  2. additiondiluted with DCM
  3. washwashed with water (2×), sodium carbonate (2×)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column

출처 및 근거

ORD 기록
ord-a386e4be99ec4f7baac19734456a06f2
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599902B2

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