Thiomorpholine → 1-[3-Chloro-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-6-(2-thiomorpholin-4-yl-ethoxy)-phenyl]-ethanone

HRID 219474

반응식

HRID 219474 반응식
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([O:21][CH3:22])[C:8]([Cl:23])=[C:7]([CH3:24])[C:6]=1[C:25](=[O:27])[CH3:26].[NH:28]1[CH2:33][CH2:32][S:31][CH2:30][CH2:29]1>>[Cl:23][C:8]1[C:7]([CH3:24])=[C:6]([C:25](=[O:27])[CH3:26])[C:5]([O:4][CH2:3][CH2:2][N:28]2[CH2:33][CH2:32][S:31][CH2:30][CH2:29]2)=[C:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]=1[O:21][CH3:22]

참가 물질

3

반응물 2

HCID 67164ThiomorpholineHCID 595834951-[2-(2-Bromo-ethoxy)-5-chloro-4-methoxy-6-methyl-3-(3-phenyl-propoxy)-phenyl]-ethanone

생성물 1

HCID 252543751-[3-Chloro-4-methoxy-2-methyl-5-(3-phenyl-propoxy)-6-(2-thiomorpholin-4-yl-ethoxy)-phenyl]-ethanone수율 79%

반응 조건

온도
65 °C

실험 절차

Example 34b (201 mg, 0.44 mmol) and thiomorpholine were reacted as described under the General Procedure B (except heated to 65° C.) and the crude was purified by flash chromatography (silica-gel, EtOAc/hexane 1:4) yielding the title compound (166 mg, 79%) as an oil. 1H NMR (300 MHz, CDCl3) δ 7.33-7.02 (m, 5H), 4.13-4.06 (m, 4H); 3.88 (s, 3H); 2.82 (dd, J=9.3, 7.5 Hz, 2H); 2.76-2.73 (m, 4H); 2.68-2.64 (m, 6H); 2.52 (s, 3H); 2.20 (s, 3H), 2.13-2.03 (m, 2H). MS (ES+) m/z 478 (M+H+).

후처리

  1. customthe crude was purified by flash chromatography (silica-gel, EtOAc/hexane 1:4)

출처 및 근거

ORD 기록
ord-4e045b7e43ac4e468c690edeaadca965
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202513B2

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