N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2,6-difluorophenyl)acetamide → 2-[4-(5-ethoxy-6-oxo-1H-pyridin-3-yl)-2,6-difluorophenyl]-N-[4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl]acetamide

HRID 1428591노트

반응식

HRID 1428591 반응식
C([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:48])[CH2:20][C:21]2[C:26]([F:27])=[CH:25][C:24]([C:28]3[CH:29]=[N:30][C:31]([O:37]CC4C=CC(OC)=CC=4)=[C:32]([O:34][CH2:35][CH3:36])[CH:33]=3)=[CH:23][C:22]=2[F:47])=[CH:14][C:13]=1[C:49]([F:52])([F:51])[F:50])C1C=CC=CC=1>CO.[Pd]>[CH2:35]([O:34][C:32]1[C:31](=[O:37])[NH:30][CH:29]=[C:28]([C:24]2[CH:25]=[C:26]([F:27])[C:21]([CH2:20][C:19]([NH:18][C:15]3[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[C:13]([C:49]([F:50])([F:52])[F:51])[CH:14]=3)=[O:48])=[C:22]([F:47])[CH:23]=2)[CH:33]=1)[CH3:36]

참가 물질

4

반응물 1

HCID 90416829N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2,6-difluorophenyl)acetamide

생성물 1

HCID 784264712-[4-(5-ethoxy-6-oxo-1H-pyridin-3-yl)-2,6-difluorophenyl]-N-[4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl]acetamide수율 14.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of N-(4-(2-(benzyloxy)ethoxy)-3-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2,6-difluorophenyl)acetamide (70 mg, 0.097 mmol) and Pd/C (10.31 mg, 0.097 mmol) in MeOH (10 mL) was stirred under a H2 atmosphere for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was filtered. The filtrate was concentrated to give the crude product, which was purified by preparative HPLC to yield a white solid of 2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2,6-difluorophenyl)-N-(4-(2-hydroxyethoxy)-3-(trifluoromethyl)phenyl)acetamide (7 mg, 0.014 mmol, 14.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.83 (d, J=2.4 Hz, 1H), 7.71 (d, J=6.8 Hz, 1H), 7.36 (d, J=2.0 Hz, 1H), 7.24 (dd, J=3.0, 5.4 Hz, 3H), 7.16 (d, J=9.0 Hz, 1H), 4.07-4.20 (m, 4H), 3.87 (t, J=5.0 Hz, 2H), 3.81 (s, 2H), 1.46 (t, J=7.06 Hz, 3H); ES-LCMS m/z 513.1 (M+H).

후처리

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. customto give the crude product, which
  4. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-12d3a0dd5b4c4d388d75bc8b50372f43
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937071B2

반응 노트

불러오는 중…