Triethylamine → HCID 19593184, compound

HRID 613427Notes

Reaction equation

[C:1]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]2[CH:12]=[C:11]([CH:13]3[CH:15]([C:16](O)=[O:17])[CH2:14]3)[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O.C([N:39](CC)CC)C>>[C:19]1([C:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH:12]=[C:11]([CH:13]3[CH:15]([C:16]([NH2:39])=[O:17])[CH2:14]3)[N:10]=[CH:9]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

HCID 19593132HCID 19593132, compound

Product 1

HCID 19593184HCID 19593184, compound

Procedure

According to the foregoing reaction scheme I 3-[1-(triphenylmethyl)-1H-imidazol4-yl]-cyclopropanecarboxylic acid (1), prepared as a racemic mixture of trans cyclopropanes using the method of Burger, et al., J. Med. Chem., (1970), 13: 33-35, is converted to an activated ester through the action of ethyl chloroformate and triethylamine. The activated ester is reacted in situ with amine (2) to provide the 3-[1-(triphenylmethyl)-1H-imidazol-4-yl]-cyclopropanecarboxamide (3). The trityl group can be removed with acid, preferably aqueous 2N HCl, to give 3-[1H-imidazol-4-yl]-cyclopropanecarboxamide (4).

Sources & evidence

ORD record: ord-261bd64f556540c380256a0e36be0f86
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008240

Reaction notes

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