Tert-butyl 3-{6-{[bis(3-methylbutyl)amino]carbonyl}-2-[(4-nitrophenyl)amino]-1H-benzimidazol-1-yl}propylcarbamate → tert-butyl 3-(2-[(4-aminophenyl)amino]-6-{[bis(3-methylbutyl)amino]carbonyl}-1H-benzimidazol-1-yl)propylcarbamate

HRID 1784312Notes

Reaction equation

[CH3:1][CH:2]([CH3:43])[CH2:3][CH2:4][N:5]([CH2:38][CH2:39][CH:40]([CH3:42])[CH3:41])[C:6]([C:8]1[CH:9]=[CH:10][C:11]2[N:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[N:13]([CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:12]=2[CH:37]=1)=[O:7]>C(OCC)(=O)C.CO.[Pd]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:14]2[N:13]([CH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[C:12]3[CH:37]=[C:8]([C:6]([N:5]([CH2:4][CH2:3][CH:2]([CH3:43])[CH3:1])[CH2:38][CH2:39][CH:40]([CH3:41])[CH3:42])=[O:7])[CH:9]=[CH:10][C:11]=3[N:15]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 20 °C

Procedure

Tert-butyl 3-{6-{[bis(3-methylbutyl)amino]carbonyl}-2-[(4-nitrophenyl)amino]-1H-benzimidazol-1-yl}propylcarbamate (580 mg) in solution in a mixture of ethyl acetate/methanol 3:1 (40 ml), and 10% palladium on carbon (58 mg) are introduced into an autoclave. After stirring for 15 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C., the catalyst is eliminated by filtration on celite and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of a foam (480 mg; 87% yield).

Workup

additionare introduced into an autoclave
filtrationthe catalyst is eliminated by filtration on celite
concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record: ord-92cc75313c9f4563914bdda9ed66a809
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501525B2

Reaction notes

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