Hydrochloric Acid → HCID 178429032, compound
Reaction equation
[O:1]1[CH2:5]CCC1.[CH3:6][C:7]1[N:12]=[C:11]([C:13]([NH2:15])=O)[CH:10]=[C:9]([O:16][CH:17]([CH3:22])[C:18]([F:21])([F:20])[F:19])[CH:8]=1.[N:23]12CCCN=C1CCCCC2.Cl.[OH2:35]>>[CH3:6][C:7]1[N:12]=[C:11]([C:13]2[NH:23][O:35][C:5](=[O:1])[N:15]=2)[CH:10]=[C:9]([O:16][CH:17]([CH3:22])[C:18]([F:21])([F:20])[F:19])[CH:8]=1Participants
6
Procedure
To 5 ml of tetrahydrofuran were added 0.63 g of 6-methyl-4-(2,2,2-trifluoro-1-methylethoxy)pyridine-2-carboxamide=oxime and 0.51 g of 1,1′-carbonylimidazole, and the mixture was stirred at room temperature for 2 hours. Thereafter, 0.47 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added, and the mixture was stirred. To the reaction solution were added water and 10% HCl, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.64 g of 3-[6-methyl-4-(2,2,2-trifluoro-1-methylethoxy)pyridin-2-yl]-1,2,4-oxadiazol-5-one (present compound (30)).
Workup
- stirringthe mixture was stirred
- extractionthe resultant solution was extracted with ethyl acetate three times
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f3113fa497cd4844ba1140bd972d723f
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318776B2
Reaction notes
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