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

HRID 713793Notes

Reaction equation

HRID 713793 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[CH:20]=[CH:19][C:15]([C:16](O)=O)=[CH:14][C:13]=1[F:21].N>>[Cl:11][C:12]1[CH:20]=[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)=[CH:14][C:13]=1[F:21]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 27365364-Chloro-3-fluorobenzoic acid

Product 1

HCID 670260055-(4-Chloro-3-fluorophenyl)-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-3-fluorobenzoic acid (Aldrich). 1H NMR (300 MHz, CD3OD) δ 7.64 (ddd, J=7.9, 5.0, 1.0 Hz, 1H), 7.78 (dd, J=8.3, 7.5 Hz, 1H), 8.07 (ddd, J=8.3, 2.0, 0.8 Hz, 1H), 8.12 (dd, J=9.5, 2.0 Hz, 1H), 8.55 (dt, J=7.9, 2.0 Hz, 1H), 8.74 (dd, J=5.0, 1.8 Hz, 1H), 9.28-9.30 (m, 1H) ppm; MS (DCl/NH3) m/z 276 (M+H)+.

Sources & evidence

ORD record
ord-2ab66f4c30424886819dca90025ac557
Source dataset
uspto-grants-2015_11
Patent number
US09186407B2

Reaction notes

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