5-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acid pentafluorophenyl ester → [2-({2-[5-(3-Carbamimidoyl-propylcarbamoyl)-1-(3-methyl-butyl)-1H-pyrrol-3-ylcarbamoyl]-1H-indole-5-carbonyl}-amino)-ethyl]-carbamic acid tert-butyl ester
Reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[N:11]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)=[O:9])(=[NH:3])[NH2:2].FC1C([O:30][C:31]([C:33]2[NH:34][C:35]3[C:40]([CH:41]=2)=[CH:39][C:38]([C:42](=[O:54])[NH:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:37][CH:36]=3)=O)=C(F)C(F)=C(F)C=1F>>[C:50]([O:49][C:47](=[O:48])[NH:46][CH2:45][CH2:44][NH:43][C:42]([C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33]([C:31](=[O:30])[NH:15][C:13]1[CH:14]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][CH2:5][CH2:4][C:1](=[NH:3])[NH2:2])[N:11]([CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH:12]=1)=[CH:41]2)=[O:54])([CH3:53])([CH3:51])[CH3:52]Participants
3
Reactant 2
Product 1
Procedure
1-(3-Methyl-butyl)-4-nitro-1H-pyrrole-2-carboxylic acid (3-carbamimidoyl-propyl)-amide (prepared by the methods described in Dyatkina et al. J. Med. Chem., 45:805–817, 2002) was reduced to its amine by hydrogenation according to the procedure for 97. The amine was then coupled with compound 33 according to the similar procedure for preparation of compound 95 to give compound 101 in 58% yield. MS: 609.33 (M+H+).
Sources & evidence
- ORD record
- ord-45dcb7f6149b4946b7469f0ab798de48
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141680B2
Reaction notes
Loading…