Acetic Acid → HCID 66608424, compound

HRID 1398203Notes

Reaction equation

CS[C:3]1[C@@:8]([O:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=2)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][N:4]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[C:36]1[O:40][C:39]([CH3:41])=[N:38][CH:37]=1)[C:29]([NH:31][NH2:32])=O.C(O)(=O)C>C(OCC)(=O)C>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:29]2[N:4]3[CH2:5][CH2:6][CH2:7][C@:8]([O:14][C:15]4[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([F:23])[CH:16]=4)([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:3]3=[N:32][N:31]=2)[CH:33]=[CH:34][C:35]=1[C:36]1[O:40][C:39]([CH3:41])=[N:38][CH:37]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To ethyl (3S)-2-(methylsulfanyl)-3-(3,4,5-trifluorophenoxy)-3,4,5,6-tetrahydropyridine-3-carboxylate (702 mg) and 3-methoxy-4-(2-methyl-1, 3-oxazol-5-yl)benzohydrazide (500 mg) was added acetic acid (3 mL), and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 10% aqueous potassium carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and purified by silica gel column chromatography (NH, ethyl acetate). The crudely-purified product was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (933 mg).

Workup

washthe mixture was washed with 10% aqueous potassium carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
custompurified by silica gel column chromatography (NH, ethyl acetate)
customThe crudely-purified product was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-22c1588a7b5a49e28de0276cef09daf2
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901309B2

Reaction notes

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