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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 2079095
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HRID 2079095 반응식
[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
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참가 물질

9

반응물 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

생성물 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 acid
수율 93.2%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f6939bd0ef5b452fb2fa6b939ce9d8e7
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928228B2

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