4-Fluoropiperidine hydrochloride → 1-{3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-[2-(4-fluoro-piperidin-1-yl)-ethoxy]-4-methoxy-2-methyl-phenyl}-ethanone

HRID 219456

반응식

HRID 219456 반응식
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].Cl.[F:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:35]2[CH2:36][CH2:37][CH:32]([F:31])[CH2:33][CH2:34]2)=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

참가 물질

3

반응물 2

HCID 27591584-Fluoropiperidine hydrochlorideHCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

생성물 1

HCID 252550051-{3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-[2-(4-fluoro-piperidin-1-yl)-ethoxy]-4-methoxy-2-methyl-phenyl}-ethanone수율 41%

실험 절차

Example 8a (89 mg, 0.18 mmol) was reacted with 4-fluoropiperidine hydrochloride (4.0 eq.) as described under General Procedure J and the crude mixture was purified by flash chromatography (silica gel, Et2O/hexane 3:2) to afford the title compound (38 mg, 41%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.66 (m, 1H), 4.05 (t, J=5.9 Hz, 2H), 3.95 (t, J=6.6 Hz, 2H), 3.83 (s, 3H), 3.00 (m, 1H), 2.64-2.59 (m, 4H), 2.50 (s, 3H), 2.44-2.36 (m, 2H), 2.18 (s, 3H), 2.05-1.97 (m, 2H), 1.94-1.81 (m, 4H), 1.30 (d, J=6.9 Hz, 3H). MS (ES+) m/z 510.2 (M+H+).

후처리

  1. customthe crude mixture was purified by flash chromatography (silica gel, Et2O/hexane 3:2)

출처 및 근거

ORD 기록
ord-38e49e0f93364d8ebe681fd6f0c8fb5c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202513B2

연결된 노트

불러오는 중…