Chlorodifluoroacetyl chloride → Rac-4-[2,2-difluoro-2-(4'-fluoro-biphenyl-4-yloxy)-acetylamino]-thiophene-3-carboxylic acid

HRID 14619Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][S:7][CH:6]=1)=[O:4].Cl[C:12]([F:17])([F:16])[C:13](Cl)=[O:14].[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1>>[F:16][C:12]([F:17])([O:31][C:28]1[CH:27]=[CH:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[CH:30][CH:29]=1)[C:13]([NH:10][C:9]1[C:5]([C:3]([OH:2])=[O:4])=[CH:6][S:7][CH:8]=1)=[O:14]

Participants

Reactant 3

HCID 67713Chlorodifluoroacetyl chloride

HCID 3454204-Fluoro-4'-hydroxybiphenyl

HCID 2777610Methyl 4-aminothiophene-3-carboxylate

Product 1

HCID 16068689Rac-4-[2,2-difluoro-2-(4'-fluoro-biphenyl-4-yloxy)-acetylamino]-thiophene-3-carboxylic acid

Procedure

In analogy to Example 58, the title compound was prepared using 4-amino-thiophene-3-carboxylic acid methyl ester, chlorodifluoroacetyl chloride and 4-fluoro-4′-hydroxybiphenyl. MS (m/e): 406.1 (M−H).

Sources & evidence

ORD record: ord-97d98d3be3ea433fbff47711219bf1d3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732452B2

Reaction notes

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