1-Hydroxybenzotriazole → HCID 54058721, compound

HRID 651187Notes

Reaction equation

HRID 651187 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:36][O:37][C:38](=[O:52])[CH2:39][NH:40][C:41](=[O:51])[CH:42]([NH2:50])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(#N)C>[CH3:36][O:37][C:38](=[O:52])[CH2:39][NH:40][C:41](=[O:51])[CH:42]([NH:50][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:13])[CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 351658Methyl 2-(2-amino-3-phenylpropanamido)acetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54058721HCID 54058721, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent4×

Conditions

Temperature
80 °C

Procedure

To 5.0 mmol of 5-chloro-1H-indole-2-carboxylic acid (50 mL of a 0.1 M solution in acetonitrile) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (50 mL of a 0.10 M solution in acetonitrile, 5.0 mmol), 1-hydroxybenzotriazole (50 mL of a 0.10 M solution in acetonitrile, 5.0 mmol), followed by (2-amino-3-phenyl-propionylamino)-acetic acid methyl ester (50 mL of a 0.10 M solution in acetonitrile, 5.0 mmol). The reaction was agitated overnight at 80° C. and then concentrated to dryness to give the title compound.

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-40966ff33508425da6d0f9cd2dc63164
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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