Sodium Azide → 4'-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide

HRID 31424Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([CH3:24])=[C:22]([F:25])[CH:21]=[C:20]([C:26]([NH:28][CH:29]4[CH2:31][CH2:30]4)=[O:27])[CH:19]=3)=[CH:14][CH:13]=2)=[N:9][N:8]=1>O.CN(C=O)C.C(O)C>[N:1]([CH2:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([CH3:24])=[C:22]([F:25])[CH:21]=[C:20]([C:26]([NH:28][CH:29]4[CH2:30][CH2:31]4)=[O:27])[CH:19]=3)=[CH:14][CH:13]=2)=[N:9][N:8]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of sodium azide (40 mg) in water (3.5 ml) was added to (4′-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (200 mg) in DMF (1.5 ml) and ethanol (7 ml) and the reaction mixture stirred for 5 hours at 90° C. The reaction was concentrated under vacuum and the residue partitioned between water (15 ml) and chloroform (15 ml) and the aqueous extracted with chloroform (2×15 ml). The combined organic extracts were dried (magnesium sulphate), and the solvent evaporated under vacuum to give 4′-[5-(azidomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

concentrationThe reaction was concentrated under vacuum
customthe residue partitioned between water (15 ml) and chloroform (15 ml)
extractionthe aqueous extracted with chloroform (2×15 ml)
dry with materialThe combined organic extracts were dried (magnesium sulphate)
customthe solvent evaporated under vacuum

Sources & evidence

ORD record: ord-5342d0f3f4284b378fcff678151285a4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425555B2

Reaction notes

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