Diisopropylethylamine → HCID 178513761, compound

HRID 12446Notes

Reaction equation

[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.CC[N:12](C(C)C)C(C)C>>[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([NH2:12])=[O:9])[N:6]=1

Participants

Reactant 2

HCID 81531Diisopropylethylamine

HCID 178524799HCID 178524799, compound

Product 1

HCID 178513761HCID 178513761, compound

Procedure

Scheme 2 illustrates the synthesis of compounds 9 and 10. Lithiation of compound 6 with n-BuLi followed by the addition of carbon dioxide affords 2-chloro-imidazole-4-carboxylic acid 7. Reaction of acid 7 with amine 2 in the presence of DMC and DIEA furnishes 2-chloro-imidazole-4-carboxamide 8, which undergoes Suzuki coupling reaction with arylboronic acid to give 2-aryl-imidazole-4-carboxamide 9. Reduction of amide 9 with Alane-N,N-dimethylethylamine complex gives compound 10. Alternatively, compound 10 is prepared from hydroxymethylimidazoles 12 via SOCl2 treatment and subsequent alkylation reaction with amine 2.

Sources & evidence

ORD record: ord-4d92171a582840429dbb0306b8c4e10e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728009B1

Reaction notes

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