Potassium Carbonate → HCID 178522113, compound

HRID 85103Notes

Reaction equation

HRID 85103 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[C:18]2[N:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[NH:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)=[O:9].C1C=C(Cl)C=C(C(OO)=[O:37])C=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[F:27][C:25]([F:28])([F:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[NH:15][C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N+:1]=3[O-:37])=[O:9])[C:18]=2[N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67203708N-(pyridin-2-yl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide

Product 1

HCID 178522113HCID 178522113, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(pyridin-2-yl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide (10; 100 mg, 0.26 mmol) in CH2Cl2 (10 mL) was added mCPBA (140 mg, 0.81 mmol) under nitrogen. The mixture was stirred at room temperature for 12 h. A saturated aqueous solution of K2CO3 (10 mL) was added and the mixture was extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried (Na2SO4), concentrated under reduced pressure. The resulting residue was purified by chromatography (CH2Cl2:methanol=20:1) to give 2-(2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamido)pyridine 1-oxide (Compound 329) (60.0 mg, 58%) as a colorless solid. MS (ESI) calcd for C20H13F3N4O2: 398.10; found: 399 [M+H].

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×10 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography (CH2Cl2:methanol=20:1)

Sources & evidence

ORD record
ord-e4c644a00c804731a05564ebf8ef5a86
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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