Ethyl difluoroacetate → 5-(5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acid

HRID 1397397Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])[NH2:4].[F:14][CH:15]([F:21])[C:16](OCC)=O>>[F:14][CH:15]([F:21])[C:16]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[N:7][CH:8]=[C:9]([CH:13]=2)[C:10]([OH:12])=[O:11])[N:4]=1

Participants

Reactant 2

HCID 9961Ethyl difluoroacetate

HCID 866775965-(N'-hydroxycarbamimidoyl)nicotinic acid

Product 1

HCID 673239365-(5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinic acidYield 30%

Procedure

This compound was synthesized from 5-(N′-hydroxycarbamimidoyl)nicotinic acid using ethyl difluoroacetate as described in example 1 step 5 (100 mg, yield 30%). 1H NMR (400 MHz, DMSO-d6) δ 13.94 (br s, 1H), 9.40 (d, J=2.1 Hz, 1H), 9.28 (d, J=2.1 Hz, 1H), 8.76-8.75 (t, J=2.1 Hz, 1H), 7.73-7.47 (m, 1H). MS (ESI) m/z: Calculated for C9H6F2N3O3: 241.03. found: 241.8 (M+H)+.

Sources & evidence

ORD record: ord-884a746a49194b90b52da1553a5fc540
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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