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 577509노트

반응식

HRID 577509 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: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

참가 물질

3

반응물 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

생성물 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)-one수율 17.8%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-a9e332bf9a8d4608b33031a699f60a92
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

반응 노트

불러오는 중…