Ethanol → 4-(5-Ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690739노트

반응식

HRID 1690739 반응식
Cl[CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1)[CH3:31]

참가 물질

4

반응물 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 669066914-(5-Chloromethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

생성물 1

HCID 577810774-(5-Ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

실험 절차

To a solution of 4-(5-chloromethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.150 g, 0.516 mmol), prepared as described in Example 18, in anhydrous ethanol (5 mL) is added diisopropylethyl amine (0.100 g, 0.77 mmol) and the mixture is stirred at reflux overnight. The mixture is purified by semi-preparative reverse phase HPLC to give 4-(5-ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 301.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.26 (s, 3 H), 1.29 (t, J=6.1 Hz, 3 H), 1.54 (s, 3 H), 3.62 (br. s, 2 H), 4.70 (br. s, 2 H), 5.59 (s, 1 H), 7.02 (s, 1 H), 7.29 (br. s, 1 H), 7.52 (d, J=7.8 Hz, 1 H), 7.63 (td, J=7.8, 1.3 Hz, 1 H), 7.74 (td, J=7.6, 1.3 Hz, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1H).

후처리

  1. temperatureat reflux overnight
  2. customThe mixture is purified by semi-preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-be7afdd112e14dc99f6147ddb0ea255c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153674B2

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