Acetic Acid → 2-(3-{(3,4-Dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid

HRID 1698701Notes

Reaction equation

HRID 1698701 reaction equation
[B-]C#N.[Na+].C(O)(=O)C.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C:19](=[N:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[N:46]=[C:45]([CH3:47])[O:44][N:43]=3)=[CH:38][CH:37]=2)[C:20]2[NH:24][C:23](=[O:25])[N:22]([C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[C:28]([OH:30])=[O:29])[N:21]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].Cl>CO.O.C(OCC)(=O)C.C1COCC1>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:19]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[N:46]=[C:45]([CH3:47])[O:44][N:43]=3)=[CH:38][CH:37]=2)[C:20]2[NH:24][C:23](=[O:25])[N:22]([C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[C:28]([OH:30])=[O:29])[N:21]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 20587905Sodium cyanoborohydride [MI]HCID 1361737382-(3-{(3,4-Dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid

Product 1

HCID 1361736272-(3-{(3,4-Dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acidYield 73.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 16.3 mg of sodium cyanotrihydroborate and 0.0074 ml of acetic acid to a solution of 34 mg of 2-(3-{(3,4-dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid in 6 ml of a methanol:THF=2:1 mixed solvent, the mixture was stirred at room temperature for 20 hours. Next, 0.1 ml of 5N hydrochloric acid was added to the reaction mixture and the mixture was stirred at room temperature for 10 minutes, after which 10 ml of ethyl acetate and 5 ml of water were added and filtration was performed with celite. The aqueous layer was extracted with 10 ml of ethyl acetate, and the organic layers were combined and dried over anhydrous magnesium sulfate. The desiccating agent was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by NAM silica gel column chromatography (methanol-dichloromethane) to give the title compound (25 mg) as a white solid.

Workup

  1. filtrationfiltration
  2. extractionThe aqueous layer was extracted with 10 ml of ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by NAM silica gel column chromatography (methanol-dichloromethane)

Sources & evidence

ORD record
ord-193bb02daee2425cbff146099074dfef
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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