Sodium Chloride → HCID 44176604, compound

HRID 1673050Notes

Reaction equation

HRID 1673050 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:36](OC(=O)C)(=O)[CH3:37].C([O-])([O-])=O.[Na+].[Na+].[Na+].[Cl-]>N1C=CC=CC=1>[CH3:36][C:37]1[O:23][C:22]([C:20]2[N:19]=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:33])[F:34])[N:17]([C:14]3[CH:15]=[CH:16][C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=4)=[CH:12][CH:13]=3)[CH:21]=2)=[N:24][N:25]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 59240015HCID 59240015, compound

Product 1

HCID 44176604HCID 44176604, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

To a 0° C. solution of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carbohydrazide (192 mg, 0.383 mmol) in 1 mL pyridine was added acetic anhydride (0.085 mL, 0.767 mmol). The ice bath was removed and the reaction stirred for 1 h. The solvent was removed in vacuo and approximately 3 mL of PPA was added to the flask. The reaction was heated to 120° C. for 2 h. Upon completion of the reaction 10 mL ice water was added to the reaction. The mixture was transferred to a 150 mL Erlenmeyer flask and neutralized with 2M Na2CO3. Solid NaCl was added the solution was extracted with ethyl acetate 3×20 mL. The combined organic layers were dried with MgSO4 and the solvent was removed in vacuo. The residue was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 2-methyl-5-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1,3,4-oxadiazole (25 mgs, 13%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 8.53 (s, 1H), 8.15-8.14 (m, 1H), 8.05-8.02 (m, 1H), 7.93-7.90 (m, 1H), 7.88-7.83 (m, 3H), 7.75-7.71 (m, 3H), 7.69-7.66 (m, 1H), 7.41 (d, J=8.58 Hz, 2H), 3.28 (s, 3H), 2.58 (s, 3H); MS (ES): 525.0 [M+H]+ and 547.3 [M+Na]+.

Workup

  1. customThe ice bath was removed
  2. customThe solvent was removed in vacuo and approximately 3 mL of PPA
  3. additionwas added to the flask
  4. customUpon completion of the reaction 10 mL ice water
  5. additionwas added to the reaction
  6. extractionwas extracted with ethyl acetate 3×20 mL
  7. dry with materialThe combined organic layers were dried with MgSO4
  8. customthe solvent was removed in vacuo
  9. customThe residue was absorbed onto silica
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-23fa84525aa447d199a2dca98450a0c7
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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