(2-{[1-(5-Nitro-1H-indol-2-yl)-methanoyl]-amino}-ethyl)-propyl-carbamic acid dimethyl-ethyl ester → 1H-indole-2,5-dicarboxylic acid bis-{[2-(2-propylamino-ethylcarbamoyl)-1H-indol-5-yl]-amide}
Reaction equation
CC(OC(=O)[N:7]([CH2:11][CH2:12][NH:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([N+:25]([O-])=O)=[CH:20][CH:19]=2)=[O:15])[CH2:8][CH2:9][CH3:10])(C)C.C([NH:31][CH2:32][CH2:33][NH:34][C:35]([C:37]1[NH:38][C:39]2[C:44]([CH:45]=1)=[CH:43][C:42]([NH:46][C:47]([C:49]1[NH:50][C:51]3[C:56]([CH:57]=1)=[CH:55][C:54]([C:58](NC1C=C4C(=CC=1)NC(C(=O)NCCNCC)=C4)=[O:59])=[CH:53][CH:52]=3)=[O:48])=[CH:41][CH:40]=2)=[O:36])C.F[C:79]1[C:84](NC(C2NC3C(C=2)=CC(C(NC2C(F)=C(F)C(F)=C(F)C=2F)=O)=CC=3)=O)=C(F)C(F)=C(F)[C:80]=1F>>[CH2:80]([NH:31][CH2:32][CH2:33][NH:34][C:35]([C:37]1[NH:38][C:39]2[C:44]([CH:45]=1)=[CH:43][C:42]([NH:46][C:47]([C:49]1[NH:50][C:51]3[C:56]([CH:57]=1)=[CH:55][C:54]([C:58]([NH:25][C:21]1[CH:22]=[C:23]4[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:14](=[O:15])[NH:13][CH2:12][CH2:11][NH:7][CH2:8][CH2:9][CH3:10])=[CH:24]4)=[O:59])=[CH:53][CH:52]=3)=[O:48])=[CH:41][CH:40]=2)=[O:36])[CH2:79][CH3:84]Participants
4
Reactant 3
Product 1
Procedure
Compound 82 (131.2 mg, 0.336 mmol) was reduced to 83 by hydrogenation according to general procedure A in Example 10. Similar procedure as described for the preparation of 76 from condensation of compound 83 with 1H-indole-2,5-dicarboxylic acid bis-(pentafluorophenyl-amide) 74 (45 mg, 0.084 mmol) followed deprotection of Boc group and purification by HPLC gave 80 (39.4 mg, 63%). ESI MS: 690.31 (M+H+), 345.66 (M/2+H+).
Workup
- customdeprotection of Boc group and purification by HPLC
Sources & evidence
- ORD record
- ord-544de50225d94d77acd652fe128025ac
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07064218B2
Reaction notes
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