Isoniazid → 4-(5-{2-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]propyl}-4-methyl-4H-1,2,4-triazol-3-yl)pyridine

HRID 639839Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:25])[CH2:20][C:21]([NH:23][CH3:24])=O)[N:18]=2)[CH:11]=[CH:12][CH:13]=1.N1C(C)=CC=CC=1C.[C:34]([NH:42][NH2:43])(=O)[C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[N:15]=[N:16][N:17]([CH:19]([CH3:25])[CH2:20][C:21]3[N:23]([CH3:24])[C:34]([C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)=[N:42][N:43]=3)[N:18]=2)[CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Oxalylchloride (2M in DCM, 0.28 mL, 0.55 mmol) was dropwise added during 5 minutes to a solution of 3-[5-(3-chlorophenyl)-2H-tetrazol-2-yl]-N-methylbutanamide (140 mg, 0.5 mmol) and 2,6-lutidine (0.12 mL, 1 mmol) in DCM (5 mL) at 0° C. The mixture was stirred at 0° C. for 1 h and isonicotinic acid hydrazide (103 mg, 0.75 mmol) was added. DCM was evaporated after 4 h stirring at r.t. Sat. aq. NaHCO3 (10 mL) was added to the residue and the mixture was refluxed for 16 h. The reaction was allowed to attain r.t., followed by extracted with CHCl3 (3×20 mL). The combined organic phases were dried (MgSO4), concentrated and purified by prep HPLC to yield the title compound (3 mg, 2%).

Workup

customDCM was evaporated after 4 h
stirringstirring at r.t
additionSat. aq. NaHCO3 (10 mL) was added to the residue
temperaturethe mixture was refluxed for 16 h
customto attain r.t.
extractionby extracted with CHCl3 (3×20 mL)
dry with materialThe combined organic phases were dried (MgSO4)
concentrationconcentrated
custompurified by prep HPLC

Sources & evidence

ORD record: ord-3f0ba60098e243fe8eb264b578fdf3dc
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691892B2

Reaction notes

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