2-Chloroisonicotinic acid → 2-Chloro-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridine

HRID 1983132Notes

Reaction equation

HRID 1983132 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([NH:15][NH2:16])=[O:14].[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][N:26]=1)[C:21](O)=O>>[Cl:17][C:18]1[CH:19]=[C:20]([C:21]2[O:14][C:13]([C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])=[N:15][N:16]=2)[CH:24]=[CH:25][N:26]=1

Participants

3

Reactant 2

HCID 2369852-Chloroisonicotinic acidHCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazide

Product 1

HCID 866135792-Chloro-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-pyridineYield 47%

Procedure

As described for example 2, 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (1.92 mg, 8.83 mmol) was converted using 2-chloroisonicotinic acid instead of o-toluic acid to the title compound (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20, 1.41 mg, 47%) which was obtained as a white solid. MS: m/e=339.1 [M+H]+.

Sources & evidence

ORD record
ord-52a531de71b24fbc986cb932e0e25f89
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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