Ammonia → 5-(4-Chloro-2,5-difluorophenyl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

HRID 713770Notes

Reaction equation

HRID 713770 reaction equation
[OH:1][N:2]=[C:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.[Cl:11][C:12]1[C:20]([F:21])=[CH:19][C:15]([C:16](O)=O)=[C:14]([F:22])[CH:13]=1.N>>[Cl:11][C:12]1[C:20]([F:21])=[CH:19][C:15]([C:16]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[N:10]=2)=[C:14]([F:22])[CH:13]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 27332744-Chloro-2,5-difluorobenzoic acid

Product 1

HCID 670269195-(4-Chloro-2,5-difluorophenyl)-3-(pyridin-3-yl)-1,2,4-oxadiazole

Procedure

The title compound was prepared according to the procedure of Example 8 using N′-hydroxynicotinimidamide (Aldrich) and 4-chloro-2,5-difluorobenzoic acid (Aldrich). 1H NMR (300 MHz, CD3OD) δ 7.65 (ddd, J=8.0, 4.9, 1.0 Hz, 1H), 7.73 (dd, J=9.7, 5.9 Hz, 1H), 8.18 (dd, J=8.8, 6.1 Hz, 1H), 8.57 (dt, J=8.1, 1.9 Hz, 1H), 8.75 (dd, J=4.7, 1.7 Hz, 1H), 9.30 (dd, J=2.2, 0.8 Hz, 1H) ppm; MS (DCl/NH3) m/z 294 (M+H)+.

Sources & evidence

ORD record
ord-a40cc5e58de140e28f5cfab0ead3c72e
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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