3-Chloroisonicotinoyl chloride → 3-(3-Chloro-4-isopropoxyphenyl)-5-(3-chloropyridin-4-yl)-[1,2,4]-oxadiazole

HRID 1172920Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[O:22][CH:23]([CH3:25])[CH3:24])[C:15]([NH:17]O)=[NH:16]>N1C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([C:15]2[N:17]=[C:4]([C:3]3[CH:7]=[CH:8][N:9]=[CH:10][C:2]=3[Cl:1])[O:5][N:16]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH:23]([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-chloroisonicotinoyl chloride (about 2.6 mmol) (prepared by General procedure F) in pyridine (5 mL) was added 3-chloro-4-isopropoxy-N-hydroxy-benzamidine (300 mg, 1.31 mmol) (prepared by General procedure B). The mixture was heated at 100° C. overnight. The solvent was removed under reduced pressure and the crude product was purified via normal phase silica gel chromatography (0-50% ethyl acetate/heptane gradient over 30 min) to give 3-(3-chloro-4-isopropoxyphenyl)-5-(3-chloropyridin-4-yl)-[1,2,4]-oxadiazole (323 mg, 70.3%).

Workup

customThe solvent was removed under reduced pressure
customthe crude product was purified via normal phase silica gel chromatography (0-50% ethyl acetate/heptane gradient over 30 min)

Sources & evidence

ORD record: ord-12762051f2a7490d940e054b0268943c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834039B2

Reaction notes

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