Ammonium Acetate → HCID 44285152, compound

HRID 2184904Notes

Reaction equation

HRID 2184904 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](=[O:34])/[CH:23]=[C:24](\[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)/[CH3:25])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C([O-])(=O)C.[NH4+:39]>CO>[CH3:25]/[C:24](/[C:26]1[CH:27]=[C:28]([C:32]([NH2:33])=[NH:39])[CH:29]=[CH:30][CH:31]=1)=[CH:23]/[C:22](=[O:34])[NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6](=[O:8])(=[O:7])[NH2:5])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 70107072HCID 70107072, compound

Product 1

HCID 44285152HCID 44285152, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2Z)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)but-2-enamide (90 mg, 0.19 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 (144 mg, 2 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-((1Z)-1-methyl-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)-benzenecarboxamidine (35 mg, 20%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 435.1

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-57545c7de99b44439e7124f9971559cc
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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