2-(1-methyl-1H-indol-3-yl)acetic acid → HCID 136333707, compound

HRID 1953031Notes

Reaction equation

HRID 1953031 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([OH:14])=O)=[CH:3]1.Cl.[NH2:16][C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][C:29](=[O:42])[C@@H:30]([CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:41])=[N:37][N+:38]([O-:40])=[O:39])[NH2:31])=[CH:23][CH:22]=1)=[O:18].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[NH2:16][C:17]([NH:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][NH:28][C:29](=[O:42])[C@@H:30]([CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:41])=[N:37][N+:38]([O-:40])=[O:39])[NH:31][C:12](=[O:14])[CH2:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:25][CH:26]=1)=[O:18]

Participants

4

Reactant 3

HCID 2541662-(1-methyl-1H-indol-3-yl)acetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136333697HCID 136333697, compound

Product 1

HCID 136333707HCID 136333707, compoundYield 34%

Procedure

Prepared analogously to Example 69a) from 1-methyl-1H-indole-3-acetic acid, (R)-N-[[4-(aminocarbonylaminomethyl)phenyl]methyl]-N5 -[amino(nitroimino)methyl]-ornithinamide-hydrochloride and TBTU in a yield of 34% of theory. Colourless, amorphous substance, which was used in the following step without purification.

Workup

  1. customColourless, amorphous substance, which was used in the following step without purification

Sources & evidence

ORD record
ord-e39bb69d65f24b9faa81cb94bc0cffd0
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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