Dimethylformamide → 2-(4-chloro-3-(trifluoromethyl)phenyl)-N-(2-(2-(methylsulfonyl)ethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide
반응식
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:7]2=[O:12].CN(C)C=O.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][C:26]=1[C:35]([F:38])([F:37])[F:36].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]([CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:7]3=[O:12])=[O:33])=[CH:27][C:26]=1[C:35]([F:36])([F:37])[F:38]참가 물질
6
반응물 5
HCID 6228Dimethylformamide
HCID 81531Diisopropylethylamine
HCID 35198824-Chloro-3-(trifluoromethyl)phenylacetic acid
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 595796075-Amino-2-(2-(methylsulfonyl)ethyl)isoquinolin-1(2H)-one생성물 1
반응 조건
- 온도
- 50 °C
실험 절차
To a solution of 5-amino-2-(2-(methylsulfonyl)ethyl)isoquinolin-1(2H)-one (30 mg, 0.0001 mol) in N,N-dimethylformamide (700 μL, 0.009 mol) was added 2-(4-chloro-3-(trifluoromethyl)phenyl)acetic acid (51 mg, 0.00021 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (102 mg, 0.000268 mol) and N,N-diisopropylethylamine (93 μL, 0.00054 mol). The reaction mixture was stirred for 16 hours at 50° C. LC-MS analysis showed the formation of the desired product. The mixture was taken up in saturated NaHCO3 solution and washed twice with ethyl acetate. The organic layer was dried with sodium sulfate, reduced in vacuo and purified via HPLC to afford the title compound as a white solid.
출처 및 근거
- ORD 기록
- ord-4390da3f3d804cb58712a96954872e58
- 출처 데이터셋
- uspto-grants-2013_10
- 특허 번호
- US08546579B2
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