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

HRID 577479
ノート
印刷プレビュー

反応式

HRID 577479 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:30])[C:20]([O:26][CH:27]([F:29])[F:28])=[CH:21][CH:22]=3)[C:17]2=[O:31])=[C:13]([CH3:32])[CH:12]=[C:11]([CH3:33])[N:10]=1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:30][C:19]1[C:20]([O:26][CH:27]([F:29])[F:28])=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:31])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:33])=[CH:12][C:13]=1[CH3:32])[CH2:25][CH2:24]2
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 867237052-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(difluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one

生成物 1

HCID 783193628-chloro-7-(difluoromethoxy)-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-3,4-dihydroisoquinolin-1(2H)-one収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(difluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one (1i, 0.08 g, 0.169 mmol) in CH2Cl2 (10 mL) was added TFA (10 mL) at room temperature. The resulting mixture was stirred at room temperature for 4 hours. The mixture was concentrated under vacuum to give a residue, which was dissolved in CH2Cl2 (20 mL) and then washed with sat. NaHCO3 (5 mL), brine (5 mL), dried over Na2SO4, and concentrated under vacuum. The residue was purified by prep. TLC (EtOAc) to obtain the title compound (Example 1, 43.1 mg, 67%) as a white solid. 1H NMR (400 MHz, methanol-d4) δ 7.36-7.34 (m, 1H), 7.24-7.22 (m, 1H), 7.00-6.63 (m, 1H), 6.11 (s, 1H), 4.76 (s, 2H), 3.51-3.48 (m, 2H), 2.90-2.87 (m, 2H), 2.29 (s, 3H), 2.25 (s, 3H); MS 382.9 [M+1].

後処理

  1. concentrationThe mixture was concentrated under vacuum
  2. customto give a residue, which
  3. washwashed with sat. NaHCO3 (5 mL), brine (5 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by prep

出典と根拠

ORDレコード
ord-b088e31ce33348bd84b3a218bc81297b
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040515B2

反応ノート

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