Ammonium Acetate → HCID 22458318, compound

HRID 2184925Notes

Reaction equation

HRID 2184925 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH2:28][CH2:27][CH2:26][C:25]=2[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=2)=[O:23])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C([O-])(=O)C.[NH4+:41]>CO>[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([C:24]2[CH2:28][CH2:27][CH2:26][C:25]=2[C:29]2[CH:30]=[C:31]([C:35]([NH2:41])=[NH:36])[CH:32]=[CH:33][CH:34]=2)=[O:23])=[CH:19][CH:20]=1)(=[O:8])(=[O:7])[NH2:5]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 22458356HCID 22458356, compound

Product 1

HCID 22458318HCID 22458318, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl][2-(3-cyanophenyl)cyclopent-1-enyl]carboxamide (70 mg, 0.137 mmol) in 5 ml anhydrous methanol cooled in an ice bath was bubbled HCl gas until saturation was achieved. Reaction was allowed to warm to room temperature and stirred overnight. The reaction was then concentrated in vacuo and dried under hi vacuum. The dried residue was dissolved in 5 ml anhydrous methanol to which ammonium acetate (77 mg, 1 mmol) was added and the reaction heated to reflux for 2 hours. The reaction was concentrated and purified on a 2×25 cm Vydac C18 HPLC column to give 3-(2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}cyclopent-1-enyl)benzenecarboxamidine (40 mg, 63%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 461.15

Workup

  1. customwas bubbled HCl gas until saturation
  2. customReaction
  3. concentrationThe reaction was then concentrated in vacuo
  4. customdried under hi vacuum
  5. additionwas added
  6. temperaturethe reaction heated
  7. temperatureto reflux for 2 hours
  8. concentrationThe reaction was concentrated
  9. custompurified on a 2×25 cm Vydac C18 HPLC column

Sources & evidence

ORD record
ord-16402d90b48142478d7c2d672e41f70e
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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