Trifluoroacetic acid → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one

HRID 577485노트

반응식

HRID 577485 반응식
C([O:8][C:9]1[C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[C:19]([Cl:33])[C:20]([O:26][CH:27]([CH3:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:22]=3)[C:17]2=[O:34])=[C:13]([CH3:35])[CH:12]=[C:11]([CH3:36])[N:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:33][C:19]1[C:20]([O:26][CH:27]([CH3:32])[C:28]([F:31])([F:29])[F:30])=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:34])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:36])=[CH:12][C:13]=1[CH3:35])[CH2:25][CH2:24]2

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 867237102-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one

생성물 1

HCID 867237118-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one수율 34%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-[(1,1,1-trifluoropropan-2-yl)oxy]-3,4-dihydroisoquinolin-1(2H)-one (58b, 70 mg, 0.14 mmol) in CH2Cl2 (5 mL) was added TFA (1 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum. The residue was purified by column chromatography (EtOAc) to give the title compound (Example 58, 20 mg, 34%) as a white solid. 1H NMR (400 MHz, chloroform): δ 11.16 (s, 1H), 7.08-7.05 (d, 1H), 7.00-6.98 (d, 1H), 5.94 (s, 1H), 4.75 (s, 2H), 4.57-4.54 (t, 1H), 3.55 (s, 2H), 2.77 (s, 2H), 2.33-2.25 (d, 6H), 1.55 (s, 3H); MS 428.9 [M+H].

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe residue was purified by column chromatography (EtOAc)

출처 및 근거

ORD 기록
ord-241f7f74e12c497a94a43a71fd175f9b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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