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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 1698701
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HRID 1698701 반응식
[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]
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참가 물질

9

반응물 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

생성물 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 acid
수율 73.2%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-193bb02daee2425cbff146099074dfef
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163787B2

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