Hydrogen Peroxide → 1H-1,3-benzodiazole-2-carboxamide

HRID 2070895Notes

Reaction equation

HRID 2070895 reaction equation
FC(F)(F)C1C=CC(NC2N=C3C=CC=C([C:18]4[CH:19]=[CH:20][C:21]5[N:25]=[C:24]([C:26]([NH2:28])=[O:27])[NH:23][C:22]=5[CH:29]=4)N3N=2)=CC=1.OO.[OH-].[Na+].FC(F)(F)C(O)=O>CS(C)=O.O>[NH:23]1[C:22]2[CH:29]=[CH:18][CH:19]=[CH:20][C:21]=2[N:25]=[C:24]1[C:26]([NH2:28])=[O:27]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59276266HCID 59276266, compound

Product 1

HCID 4456861H-1,3-benzodiazole-2-carboxamideYield 29.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-(2-(4-(Trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-1H-benzo[d]imidazole-2-carboxamide. A mixture of 6-(2-(4-(trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-c]pyridin-5-yl)-1H-benzo[d]imidazole-2-carbonitrile (300 mg, 0.5 mmol), hydrogen peroxide (30%, 1.0 mL) and sodium hydroxide (40 mg, 1.0 mmol) in dimethylsulfoxide (5 mL) was stirred at room temperature for 3 h. The reaction mixture was poured into water (15 mL), and the mixture was extracted with ethyl acetate (15 mL×3). The combined organic layer was dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by reverse-phase preparatory HPLC (35-65% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 15 min.) to give 64244-(trifluoromethyl)phenylamino)-[1,2,4]triazolo[1,5-c]pyridin-5-yl)-1H-benzo[d]imidazole-2-carboxamide (65 mg, 29.7% yield) as a trifluoroacetic acid salt, which was converted to the hydrochloride salt with methanolic hydrochloride solution. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.19 (s, 1H), 8.37 (s, 1H), 7.95 (m, 5H), 7.73 (m, 4H), 7.29 (d, J=7.2 Hz, 1H); MS (ESI): m/z 438.1 [M+1]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (15 mL×3)
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by reverse-phase preparatory HPLC (35-65% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 15 min.)

Sources & evidence

ORD record
ord-f28bd1c725ef43228c62a17926052610
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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