Ethyl Acetate → HCID 44284734, compound

HRID 2184915Notes

Reaction equation

HRID 2184915 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:36])/[CH:23]=[C:24](\[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[N:35])[CH:29]=2)/[CH2:25][O:26][CH3:27])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[NH4+:47]>CO>[CH3:27][O:26][CH2:25]/[C:24](/[C:28]1[CH:29]=[C:30]([C:34]([NH2:35])=[NH:47])[CH:31]=[CH:32][CH:33]=1)=[CH:23]/[C:22](=[O:36])[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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 70097558HCID 70097558, compound

Product 1

HCID 44284734HCID 44284734, 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)-4-methoxybut-2-enamide (150 mg, 0.298 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 (77 mg, 1 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-(methoxymethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzenecarboxamidine (34 mg, (25%) as a fluffy off-white powder after lyophilization. ES-MS (M+H+): 465.15

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-a4910f19cfce4649aa60bd6026ba943e
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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