Water → HCID 70013674, compound

HRID 1370133Notes

Reaction equation

HRID 1370133 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[Cl:13][C:14]1[CH:15]=[C:16]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:17][N:18]1[C:22]2[CH:23]=[C:24]([C:27]#[N:28])[CH:25]=[CH:26][C:21]=2[N:20]([C@H:29]2[CH2:33][CH2:32][NH:31][CH2:30]2)[C:19]1=[O:34].O>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:17][N:18]1[C:22]2[CH:23]=[C:24]([C:27]#[N:28])[CH:25]=[CH:26][C:21]=2[N:20]([C@H:29]2[CH2:33][CH2:32][N:31]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:30]2)[C:19]1=[O:34]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70015775HCID 70015775, compound

Product 1

HCID 70013674HCID 70013674, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (27 mg) and triethylamine (24 mg) were added to a solution of 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-[(S)-pyrrolidin-3-yl]-2,3-dihydro-1H-benzimidazol-2-one (75 mg) in dichloromethane (2 mL). The reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was poured into water and extracted with a mixture of chloroform and methanol (5:1). The organic layer was washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The obtained crystals were suspended in hot ethyl acetate and then cooled with stirring. The resulting precipitate was collected by filtration and washed with ethyl acetate to give 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-[(S)-1-methanesulfonylpyrrolidin-3-yl]-2,3-dihydro-1H-benzimidazol-2-one (76 mg) as colorless crystals.

Workup

  1. extractionextracted with a mixture of chloroform and methanol (5:1)
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. temperaturecooled
  6. stirringwith stirring
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-1e6ff634ccb64ea2be7ee12ac8a0f6da
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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