Water → HCID 21876478, compound

HRID 858545Notes

Reaction equation

HRID 858545 reaction equation
[NH2:1][CH:2]([C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[O:19])=[CH:11][CH:10]=2)[C:7]2[CH:31]=[C:32]([Cl:39])[C:33]([C:35]([F:38])([F:37])[F:36])=[CH:34][C:6]=2[N:5]=1)[CH3:3].[C:40](Cl)(=[O:42])[CH3:41].O>C(Cl)Cl>[Cl:39][C:32]1[C:33]([C:35]([F:36])([F:38])[F:37])=[CH:34][C:6]2[N:5]=[C:4]([CH:2]([NH:1][C:40](=[O:42])[CH3:41])[CH3:3])[N:8]([C:9]3[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)(=[O:23])=[O:22])=[O:19])=[CH:11][CH:10]=3)[C:7]=2[CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 21876485HCID 21876485, compound

Product 1

HCID 21876478HCID 21876478, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-{[(2-{4-[2-(1-aminoethyl)-6-chloro-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamide (step 3, 100 mg, 0.17 mmol) in CH2Cl2 (12 ml) was added acetyl chloride (0.01 ml, 0.18 mmol) and stirred at room temperature for 5 h. The mixture was added water (10 ml) and extracted with CH2Cl2 (20 ml). The organic layer was washed with brine (10 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with CH2Cl2/MeOH (10:1) to afford 59 mg (53%) of the title compound as white solids.

Workup

  1. extractionextracted with CH2Cl2 (20 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with CH2Cl2/MeOH (10:1)

Sources & evidence

ORD record
ord-0c6c78eb35584b3c9f8df4fbd76888e7
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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