Indole-2-carboxylic acid → HCID 14697650, compound

HRID 704554Notes

Reaction equation

HRID 704554 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH3:10])[C:6]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:5]=2[N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]1=[O:22].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[C:32](O)=[O:33].ON1C2C=CC=CC=2N=N1>ClCCl>[Cl:15][C:13]1[CH:12]=[CH:11][C:6]2[N:7]([CH3:10])[C:8](=[O:9])[CH:2]([NH:1][C:32]([C:24]3[NH:23][C:31]4[C:26]([CH:25]=3)=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:33])[C:3](=[O:22])[N:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[CH:14]=1

Participants

5

Reactant 3

HCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 14697648HCID 14697648, compound

Product 1

HCID 14697650HCID 14697650, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.58 g (5 mmoles) of 3-amino-2,4-dioxo-7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, 0.89 g of 2-indol carboxylic acid, 1.05 g of 1-ethyl-3-(3-dimethylamino)-propyl carbodiimide, 1.02 g of 1-hydroxy benzotriazole and 50 ml of dichloromethane was stirred at ambient temperature for 18 hours and the precipitate formed was separated and washed with dichloromethane to obtain 1.36 g of the expected product melting at about 280° C. (yield 59%)

Workup

  1. customthe precipitate formed
  2. customwas separated
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-54f1ff36956f4361b6443fa0bbad65fc
Source dataset
uspto-grants-1991_01
Patent number
US04988692

Reaction notes

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