Water → HCID 49839472, compound

HRID 885459Notes

Reaction equation

HRID 885459 reaction equation
[H-].[Na+].[CH2:3]([NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:4][CH2:5][CH3:6].Cl[C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]=1.O>CN(C=O)C>[CH2:3]([N:7]([C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]=1)[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 19241N-ButylbenzenesulfonamideHCID 24758Sodium hydrideHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazole

Product 1

HCID 49839472HCID 49839472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.029 g, 0.0012 mol, 1.1 equiv) was suspended in DMF (5 mL). N-Butyl-benzenesulfonamide (0.256 g, 0.222 mL, 0.0012 mol. 1.2 equiv) was then added and stirred at room temperature for 10 minutes. To the resulting mixture was then added the 2-chloro-N-methyl benzimidazole, (0.166 g, 0.001 mol). The resulting mixture was heated to 50° C. and stirred overnight (16 hours). The resulting mixture was then poured into water (15 mL) and stirred for 1 hour. The resulting solution was extracted with DCM (20 mL) and the organic layer was separated. The organic layer was washed with 1N NaOH (20 mL), and brine (20 mL), then dried over Na2SO4 and evaporated under reduced pressure. The resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile) to yield the title compound as a yellowish solid. MS 343.4

Workup

  1. temperatureThe resulting mixture was heated to 50° C.
  2. stirringstirred overnight (16 hours)
  3. stirringstirred for 1 hour
  4. extractionThe resulting solution was extracted with DCM (20 mL)
  5. customthe organic layer was separated
  6. washThe organic layer was washed with 1N NaOH (20 mL), and brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated under reduced pressure
  9. customThe resulting residue was purified by reverse phase HPLC (eluent 60-80% acetonitrile)

Sources & evidence

ORD record
ord-942c4dd50d8748658b000f31eebf1dbf
Source dataset
uspto-grants-2012_08
Patent number
US08242157B2

Reaction notes

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