Ethyl Acetate → HCID 22458366, compound

HRID 2184913Notes

Reaction equation

HRID 2184913 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:38])/[CH:23]=[C:24](\[C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)/[C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[NH4+:49]>CO>[O:26]1[CH:27]=[CH:28][CH:29]=[C:25]1/[C:24](/[C:30]1[CH:31]=[C:32]([C:36]([NH2:37])=[NH:49])[CH:33]=[CH:34][CH:35]=1)=[CH:23]/[C:22](=[O:38])[NH:21][C:18]1[CH:19]=[CH:20][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:16][CH:17]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 22458349HCID 22458349, compound

Product 1

HCID 22458366HCID 22458366, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-3-(2-furyl)prop-2-enamide (176 mg, 0.336 mmol) in 10 ml 1:1 ethyl acetate:anhydrous methanol cooled to −78° C. 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 methyl imidate 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, treated with trifluoroacetic acid (10 ml) for 2 hrs, concentrated and purified on a 2×25 cm Vydac C18 HPLC column to give 3-((1E)-1-(2-furyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (60 mg, (37%) as a fluffy off-white powder after lyophilization. ES-MS (MA+H+): 487.15

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. additiontreated with trifluoroacetic acid (10 ml) for 2 hrs
  10. concentrationconcentrated
  11. custompurified on a 2×25 cm Vydac C18 HPLC column

Sources & evidence

ORD record
ord-10451758f1a44d838b0582e22d6b90e7
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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