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Dimethylformamide → (S)-2-(6-Chloro-1-oxo-5-(2-(4-(trifluoromethyl)phenyl)acetamido)isoquinolin-2(1H)-yl)propanamide

HRID 418495
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HRID 418495 반응식
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@@H:14]([CH3:18])[C:15]([NH2:17])=[O:16])[C:7]2=[O:13].[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN(C)C=O>>[Cl:12][C:11]1[C:2]([NH:1][C:28](=[O:29])[CH2:27][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:31])([F:19])[F:32])=[CH:26][CH:25]=2)=[C:3]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:13])[N:6]([C@@H:14]([CH3:18])[C:15]([NH2:17])=[O:16])[CH:5]=[CH:4]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58973961(S)-2-(5-Amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide

생성물 1

HCID 25013760
(S)-2-(6-Chloro-1-oxo-5-(2-(4-(trifluoromethyl)phenyl)acetamido)isoquinolin-2(1H)-yl)propanamide

반응 조건

온도
60 °C

실험 절차

A mixture of (S)-2-(5-amino-6-chloro-1-oxoisoquinolin-2(1H)-yl)propanamide (100.0 mg, 0.0003764 mol), 2-(4-(trifluoromethyl)phenyl)acetic acid (115.2 mg, 0.0005646 mol), N,N-diisopropylethylamine (163.9 μL, 0.0009409 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (357.8 mg, 0.0009409 mol) and N,N-dimethylformamide (2 mL, 0.02 mol) was stirred at 60° C. for 3 days. the solvent was removed under reduced pressure and the residue purified by reverse phase preparative HPLC to afford the product as light yellow solid.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-443b172f4e564cc2b3f3cc9f62bfc90d
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08093265B2

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