10-(benzyl(methyl)amino)-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide → N-(4-Fluorobenzyl)-3-hydroxy-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide

HRID 1093137Notes

Reaction equation

HRID 1093137 reaction equation
[CH2:1]([N:8](C)[C:9]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][N:11]1[C:18](=[O:34])[C:19]([OH:33])=[C:20]([C:22]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[O:23])[N:21]=[C:10]21)C1C=CC=CC=1>CO.[Pd]>[F:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:22]([C:20]2[N:21]=[C:10]3[C:9]4([NH:8][CH3:1])[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]4)[CH2:12][N:11]3[C:18](=[O:34])[C:19]=2[OH:33])=[O:23])=[CH:31][CH:30]=1

Participants

4

Reactant 1

HCID 5790479010-(benzyl(methyl)amino)-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide

Product 1

HCID 57904894N-(4-Fluorobenzyl)-3-hydroxy-10-(methylamino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamideYield 119.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 10-(benzyl(methyl)amino)-N-(4-fluorobenzyl)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxamide (255 mg, 0.432 mmol) in methanol (2 mL) was added Pd/C (32.2 mg, 0.030 mmol) and the mixture was stirred under hydrogen atmosphere (balloon) for 1 h. The catalyst was then filtered off, and the filtrate was evaporated under reduced pressure to afford the title compound as a white solid (200 mg, 93% yield). 1H NMR (300 MHz, DMSO-d6) δ: 12.3 (1 H, s), 9.5 (1 H, s), 7.3-7.4 (2 H, m), 7.2-7.2 (2 H, m), 4.5 (2 H, d, J=6.22 Hz), 4.0 (2 H, d, J=3.29 Hz), 2.6 (3 H, brs), 2.0-2.1 (4 H, m), 1.7-1.9 (5 H, m). LCMS (M+H)=387.17.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7ac67efdcd634853b8a6aef5b6030e94
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…