Hydrochloric Acid → N-(2,5-difluorophenyl)-2-[4-(5-ethoxy-6-oxo-1H-pyridin-3-yl)-2-fluorophenyl]acetamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:38])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[N:20][C:21]([O:27]CC3C=CC(OC)=CC=3)=[C:22]([O:24][CH2:25][CH3:26])[CH:23]=2)=[CH:14][C:13]=1[F:37].Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:38])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH3:26])[C:21](=[O:27])[NH:20][CH:19]=2)=[CH:14][C:13]=1[F:37]Participants
3
Procedure
A solution of N-(2,5-difluorophenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide (45 mg, 0.086 mmol) in HCl (MeOH (solvate), 64.6 μl, 0.258 mmol) was stirred at 20° C. for 1 h. After LCMS analysis showed the starting material had disappeared, the solvent was removed in vacuo to give crude product which was purified by preparation HPLC to afford pure product N-(2,5-difluorophenyl)-2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetamide (5.83 mg, 0.014 mmol, 16.8% yield): 1H NMR: (400 MHz, CD3OD) δ 7.86 (broad s, 1H), 7.43-7.37 (m, 5H), 7.20-7.13 (m, 1H), 6.86 (t, J=8.4 Hz, 1H), 4.20-4.15 (m, 2H), 3.88 (s, 2H), 1.48 (t, J=7.0 Hz, 3H); ES-LCMS: m/z 403.0 (M+H).
Workup
- customthe solvent was removed in vacuo
- customto give crude product which
- customwas purified by preparation HPLC
Sources & evidence
- ORD record
- ord-3ef2683d3c1a4a0a87cdcacce71f6c31
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937071B2
Reaction notes
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