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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 1161366
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1161366
[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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Komponenten

9

Edukt 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

Produkt 1

HCID 136124696
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
Ausbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-63e2a5bb833f478eb175c6e9d4838738
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07816522B2

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