Hydrochloric Acid → HCID 70015775, compound

HRID 1370131Notes

Reaction equation

HRID 1370131 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][C@H:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:17]=3[N:16]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([Cl:34])[CH:27]=3)[C:15]2=[O:35])[CH2:10]1)=O)(C)(C)C>C(OCC)(=O)C>[Cl:34][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[O:32][CH3:33])[CH2:25][N:16]1[C:17]2[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][C:18]=2[N:14]([C@H:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)[C:15]1=[O:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70013748HCID 70013748, compound

Product 1

HCID 70015775HCID 70015775, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4N-Hydrogen chloride solution in ethyl acetate (5 mL) was added to a suspension of 1-[(S)-1-tert-butoxycarbonylpyrrolidin-3-yl]-3-(3-chloro-4-methoxybenzyl)-5-cyano-2,3-dihydro-1H-benzimidazol-2-one (520 mg) in ethyl acetate (5 mL) at 0° C. The mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated in vacuo. To the residue was added an aqueous saturated sodium bicarbonate solution and ethyl acetate. The separated organic layer was washed successively with water and brine and dried over magnesium sulfate. After evaporation of the solvent, the residue was triturated with diethyl ether to give 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-[(S)-pyrrolidin-3-yl]-2,3-dihydro-1H-benzimidazol-2-one (287 mg) as amorphous powders.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the residue was added an aqueous saturated sodium bicarbonate solution and ethyl acetate
  3. washThe separated organic layer was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-40dc53996c354161a06d5ae1e1892f78
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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