p-Toluenesulfonic acid → HCID 44176495, compound
Reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([C:22]([NH:24][NH2:25])=[O:23])[N:19]=[C:18]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH:36](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[C:20]([C:22]4[O:23][CH:36]=[N:25][N:24]=4)[N:19]=[C:18]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:33])[F:34])=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]Participants
Conditions
- Temperature
- 130 °C
Procedure
To a suspension of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carbohydrazide (198 mg, 0.395 mmol) and triethyl orthoformate (1 mL, 6.01 mmol) in 1 mL xylenes was added a catalytic amount of p-toluenesulfonic acid. The reaction was heated at 130° C. for 12 h. The reaction was cooled and the mixture was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 2-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1,3,4-oxadiazole (96 mgs, 48%) as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.48 (s, 1H), 8.12 (s, 1H), 8.11-8.10 (m, 1H), 7.97-7.94 (m, 1H), 7.85-7.82 (m, 1H), 7.77-7.75 (m, 1H), 7.67 (t, J=7.83 Hz, 1H), 7.61-7.58 (m, 4H), 7.48-7.45 (m, 1H), 7.29-7.27 (m, 2H), 3.09 (s, 3H); MS (ES): 511.4 [M+H]+ and 533.0 [M+Na]+.
Workup
- temperatureThe reaction was cooled
- customthe mixture was absorbed onto silica
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-7f848ae18bf34dae9dde0071f92bd473
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998995B2
Reaction notes
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