Diisopropylethylamine → (S)-tert-Butyl 4,4-difluoro-2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate

HRID 525002노트

반응식

HRID 525002 반응식
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].[C:16]([O:20][C:21]([N:23]1[CH2:27][C:26]([F:29])([F:28])[CH2:25][C@H:24]1[C:30](O)=[O:31])=[O:22])([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C>[F:29][C:26]1([F:28])[CH2:27][N:23]([C:21]([O:20][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:22])[C@H:24]([C:30](=[O:31])[NH:1][N:2]2[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:8])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:25]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acidHCID 709224541-amino-N-phenyl-1H-pyrrole-2-carboxamide

생성물 1

HCID 86722022(S)-tert-Butyl 4,4-difluoro-2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate수율 97.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

1-Amino-N-phenyl-1H-pyrrole-2-carboxamide (500 mg, 2.48 mmol), (S)-1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (687 mg, 2.73 mmol), HATU (1.04 g, 2.73 mmol) and diisopropylethylamine (476 μl, 2.73 mmol) were dissolved in a mixture of 6 mL of dichloromethane and 6 mL of DMF and stirred at room temperature overnight. The dichloromethane was removed under vacuum and 25 mL of water were poured over the remaining solution. A precipitated appeared and the suspension was stirred overnight. The solid was filtered and washed with water to furnish 1.05 g (97% yield) of the title compound.

후처리

  1. customThe dichloromethane was removed under vacuum and 25 mL of water
  2. additionwere poured over the remaining solution
  3. stirringthe suspension was stirred overnight
  4. filtrationThe solid was filtered
  5. washwashed with water

출처 및 근거

ORD 기록
ord-0120fe6bc5ad437a855a4937b34e73e1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340547B2

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