Formamide → HCID 178518067, compound

HRID 1432198Notes

Reaction equation

C([C:3]1[C:4]([C:9]([OH:11])=O)=[C:5]([NH2:8])[S:6][CH:7]=1)C.C([O-])=O.[NH4+].[CH:16]([NH2:18])=O>>[N:8]1[C:5]2[S:6][CH:7]=[CH:3][C:4]=2[C:9]([OH:11])=[N:18][CH:16]=1

Participants

Reactant 3

HCID 713Formamide

HCID 2723923Ammonium formate

HCID 22182433Ethyl 2-amino-3-carboxythiophene

Product 1

HCID 178518067HCID 178518067, compound

Procedure

Ethyl 2-amino-3-carboxythiophene 2 is refluxed with ammonium formate and formamide to give the cyclized intermediate 3 which is then treated with thionyl chloride to afford the chloro derivative 4. Boc-protected aminopiperidine 5 is reductively alkylated with a variety of arylaldehydes 6 to provide the corresponding intermediates 7. Deprotection of 7 with trifluoroacetic acid treatment yields the free amine intermediate 8. Reflux of a mixture of the key intermediates 4 and 8 in i-propanol or acetonitrile in the presence of triethylamine yields the final compound 1.

Sources & evidence

ORD record: ord-1d530b4e1e6c40f7abbe461358d050ff
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612078B2

Reaction notes

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