Indole-4-carboxylic acid → HCID 136333699, compound

HRID 1953020Notes

Reaction equation

HRID 1953020 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=O)[C:4]=2[CH:3]=[CH:2]1.Cl.[NH2:14][C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][C:27](=[O:40])[C@@H:28]([CH2:30][CH2:31][CH2:32][NH:33][C:34]([NH2:39])=[N:35][N+:36]([O-:38])=[O:37])[NH2:29])=[CH:21][CH:20]=1)=[O:16].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[NH2:14][C:15]([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][NH:26][C:27](=[O:40])[C@@H:28]([CH2:30][CH2:31][CH2:32][NH:33][C:34]([NH2:39])=[N:35][N+:36]([O-:38])=[O:37])[NH:29][C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH:3]=[CH:2][NH:1]3)=[O:12])=[CH:23][CH:24]=1)=[O:16]

Participants

4

Reactant 3

HCID 595229Indole-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136333697HCID 136333697, compound

Product 1

HCID 136333699HCID 136333699, compoundYield 82%

Procedure

Prepared analogously to Example 69a) from 1H-indole-4-carboxylic acid, (R)-N-[[4-(aminocarbonylaminomethyl)phenyl]methyl]-N5 -[amino(nitroimino)methyl]-ornithinamide-hydrochloride and TBTU in a yield of 82% of theory.

Sources & evidence

ORD record
ord-b55a7d7292e64fcca20d619506209e00
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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