Triethylamine → HCID 44176498, compound

HRID 1673049Notes

Reaction equation

HRID 1673049 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].C(N(CC)CC)C.[C:43](N1C=CN=C1)(N1C=CN=C1)=[O:44]>C1COCC1.C(OCC)(=O)C>[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][C:43](=[O:44])[NH: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

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 59240015HCID 59240015, compound

Product 1

HCID 44176498HCID 44176498, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole-4-carbohydrazide (216 mg, 0.432 mmol), triethylamine (0.132 mL, 0.949 mmol) in 1 mL anhydrous THF was added carbonyldiimidazole (140 mg, 0.864 mmol). The reaction was stirred for 24 h at room temperature. The reaction was diluted with ethyl acetate, washed with water, brine, and dried with MgSO4. The residue was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 5-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1,3,4-oxadiazol-2(3H)-one (120 mgs, 52%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 12.48 (s, 1H), 8.39 (s, 1H), 8.15-8.14 (m, 1H), 8.04-8.01 (m, 1H), 7.93-7.90 (m, 1H) 7.87-7.82 (m, 3H), 7.75-7.70 (m, 3H), 7.66-7.64 (m, 1H), 7.38 (d, J=8.61 Hz, 2H), 3.28 (s, 3H); MS (ES): 527.3 [M+H]+ and 549.3 [M+Na]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried with MgSO4
  3. customThe residue was absorbed onto silica
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-3d7ea62d92ff43b98534adfb5649d898
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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