Ethyl Acetate → HCID 44284478, compound

HRID 2184922Notes

Reaction equation

HRID 2184922 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)/[CH:25]([CH3:27])[CH3:26])=[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][CH: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)[CH3:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 70096971HCID 70096971, compound

Product 1

HCID 44284478HCID 44284478, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of crude (2Z)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4-methylpent-2-enamide (190 mg, 0.379 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 (115 mg, 1.5 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-(methylethyl)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}vinyl)benzene carboxamidine (75 mg, 43%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 463.2.

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-8ccc148fc9934c37b0811e66af0ba98e
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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