반응 #167883

반응 방정식

benzyl(3-(benzyloxy)-2-(4-chloro-5-(4-fluorobenzyl)-1H-imidazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate

formic acid

→

title compound

수율 83.0%

10-Amino-2-[4-[(4-fluorophenyl)methyl]-1H-imidazol-2-yl]-7,8,9,10-tetrahydro-3-hydroxy-7,10-ethanopyrimido[1,2-a]azepin-4(6H)-one

수율 83.0%

용매

MeOH

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   여과the mixture was filtered through a pad of celite
3. 3
   농축concentrated
4. 4
   workup.ADDITIONThe mixture was then treated with sat. NaHCO3
5. 5
   추출extracted with dichloromethnae (×4)
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

To a solution of benzyl(3-(benzyloxy)-2-(4-chloro-5-(4-fluorobenzyl)-1H-imidazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate, Intermediate 6 (60 mg, 0.092 mmol) in MeOH (3 mL) was added formic acid (0.100 mL, 2.65 mmol) followed by 10% Pd/C (98 mg, 0.092 mmol) and the mixture stirred at 40° C. for 3 h. After cooling to room temperature, the mixture was filtered through a pad of celite and concentrated. The mixture was then treated with sat. NaHCO3, extracted with dichloromethnae (×4), dried (Na2SO4), filtered and concentrated to afford the title compound (30 mg, 83% yield) as a light purple solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.53-1.60 (m, 2H), 1.73-1.81 (m, 6H), 2.37 (br. s., 1H), 2.51-2.54 (m, 2H), 3.93-3.99 (m, 2H), 4.01 (d, J=3.66 Hz, 2H), 7.10-7.17 (m, 3H), 7.30 (dd, J=8.24, 5.80 Hz, 2H). LCMS (M+H)=396.13.

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