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 577485ノート

反応式

HRID 577485 の反応式
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

参加物

4

反応物 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

生成物 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)-one収率 34%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-241f7f74e12c497a94a43a71fd175f9b
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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