2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one → 8-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

HRID 577509ノート

反応式

HRID 577509 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:32])[C:20]([C:26]4[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=4)=[CH:21][CH:22]=3)[C:17]2=[O:33])=[C:13]([CH3:34])[CH:12]=[C:11]([CH3:35])[N:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:32][C:19]1[C:20]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[CH:21][CH:22]=[C:23]2[C:18]=1[C:17](=[O:33])[N:16]([CH2:15][C:14]1[C:9](=[O:8])[NH:10][C:11]([CH3:35])=[CH:12][C:13]=1[CH3:34])[CH2:25][CH2:24]2

参加物

3

反応物 1

HCID 867237352-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

生成物 1

HCID 867237368-chloro-2-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one収率 17.8%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (66c, 60 mg, 0.12 mmol) in TFA (3 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue purified by prep chromatography to give the title compound (Example 66, 8.5 mg, 17%) as a white solid. 1H NMR (700 MHz, DMSO-d6) δ 11.56 (br. s, 1H) 7.44 (d, J=7.70 Hz, 1H) 7.35 (d, J=7.70 Hz, 1H) 7.50 (d, J=1.76 Hz, 1H) 6.29 (d, J=1.76 Hz, 1H) 5.90 (s, 1H) 4.60 (s, 2H) 3.61 (s, 3H) 3.46-3.50 (m, 2H) 2.91 (t, J=5.83 Hz, 2H) 2.19 (s, 3H) 2.14 (s, 3H); MS 397.0 [M+1].

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue purified by prep chromatography

出典と根拠

ORDレコード
ord-a9e332bf9a8d4608b33031a699f60a92
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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