Hydrochloric Acid → HCID 68814260, compound

HRID 730590Notes

Reaction equation

HRID 730590 reaction equation
C(OC([N:8]1[C:12]2[C:13]([CH:17]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:9]1=[O:36])=O)(C)(C)C.[ClH:37].CCOCC>C(O)C>[ClH:37].[CH2:29]([N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]3[CH2:21][CH2:20][NH:19][CH2:18]3)[C:12]=2[NH:8][C:9]1=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57834986HCID 57834986, compound

Product 1

HCID 68814260HCID 68814260, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-benzyl-7-(1-tert-butoxycarbonyl-pyrrolidin-3-yl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (80 mg., 0.273 mmol) in 5 mL ethanol was heated to reflux and 2 N ethanolic hydrogen chloride was added (0.5 mL.) The reaction mixture was refluxed for 45 minutes at which point ether (2 mL) was added slowly. A solid precipitate formed on cooling and was removed by filtration to afford 40 mg of 1-benzyl-4-pyrrolidin-3-yl-1,3-dihydro-benzoimidazol-2-one hydrochloride as a tan solid. MS: 294 (M+H)+.

Workup

  1. temperatureto reflux
  2. additionwas added slowly
  3. customA solid precipitate formed
  4. temperatureon cooling
  5. customwas removed by filtration

Sources & evidence

ORD record
ord-e8250c62ba32477ab8904379742f7ecf
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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