Acetic Acid → 2-(3-{(2-Fluoro-4,5-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 1161366Notes

Reaction equation

HRID 1161366 reaction equation
[B-]C#N.[Na+].C(O)(=O)C.[F:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=1[C:20](=[N:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[N:47]=[C:46]([CH3:48])[O:45][N:44]=2)=[CH:39][CH:38]=1)[C:21]1[NH:25][C:24](=[O:26])[N:23]([C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2[C:29]([OH:31])=[O:30])[N:22]=1.Cl>CO.O.C(OCC)(=O)C.C1COCC1>[F:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=1[CH:20]([NH:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[N:47]=[C:46]([CH3:48])[O:45][N:44]=2)=[CH:39][CH:38]=1)[C:21]1[NH:25][C:24](=[O:26])[N:23]([C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2[C:29]([OH:31])=[O:30])[N:22]=1

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 20587905Sodium cyanoborohydride [MI]HCID 1361736382-(3-{(2-Fluoro-4,5-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 1361246962-(3-{(2-Fluoro-4,5-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 93.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 312 mg of sodium cyanotrihydroborate, 0.114 ml of acetic acid and 1.5 g of MS3A to a solution of 539 mg of 2-(3-{(2-fluoro-4,5-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 40 ml of a methanol:THF=1:1 mixed solvent, the mixture was stirred at room temperature for 48 hours. Next, 0.7 ml of 5N hydrochloric acid was added, the reaction mixture was stirred at room temperature for 10 minutes, ethyl acetate and water were added, and filtration was performed with celite. The aqueous layer was extracted with 50 ml of ethyl acetate and dried over anhydrous sodium 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-ethyl acetate) to give the title compound (504 mg) as a light yellow solid.

Workup

  1. filtrationfiltration
  2. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate
  3. dry with materialdried over anhydrous sodium 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-ethyl acetate)

Sources & evidence

ORD record
ord-63e2a5bb833f478eb175c6e9d4838738
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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