Ethyl Acetate → HCID 9913371, compound

HRID 2184906Notes

Reaction equation

HRID 2184906 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:37])/[CH:23]=[C:24](\[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]#[N:36])[CH:30]=2)/[C:25]([F:28])([F:27])[F:26])=[CH:17][CH:16]=1)(=[O:8])=[O:7])(C)(C)C.C(OCC)(=O)C.C([O-])(=O)C.[NH4+:48]>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](/[CH:23]=[C:24](\[C:29]2[CH:30]=[C:31]([C:35]([NH2:36])=[NH:48])[CH:32]=[CH:33][CH:34]=2)/[C:25]([F:26])([F:27])[F:28])=[O:37])=[CH:19][CH:20]=1)(=[O:7])(=[O:8])[NH2:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517165Ammonium AcetateHCID 22458317HCID 22458317, compound

Product 1

HCID 9913371HCID 9913371, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-4,4,4-trifluorobut-2-enamide (90 mg, 0.19 mmol) in 10 ml 1:1 ethyl acetate:anhydrous methanol cooled to −78° C. was bubbled HCl gas until saturation was achieved. Reaction was placed in the refrigerator at 0° C. over the weekend. 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 then treated with 10 ml trifluoroacetic acid for 2 hrs, concentrated and purified on a 2×25 cm Vydac C18 HPLC column to give 3-((1E)-2-{N-[4-(2-sulfamoylphenyl)phenyl]carbamoyl}-1-(trifluoromethyl)vinyl)benzenecarboxamidine (57 mg, 47%) as a fluffy white powder after lyophilization. ES-MS (M+H+): 489.15

Workup

  1. customwas bubbled HCl gas until saturation
  2. customReaction
  3. customwas placed in the refrigerator at 0° C. over the weekend
  4. concentrationThe reaction was then concentrated in vacuo
  5. customdried under hi vacuum
  6. additionwas added
  7. temperaturethe reaction heated
  8. temperatureto reflux for 2 hours
  9. concentrationThe reaction was concentrated
  10. additionthen treated with 10 ml trifluoroacetic acid for 2 hrs
  11. concentrationconcentrated
  12. custompurified on a 2×25 cm Vydac C18 HPLC column

Sources & evidence

ORD record
ord-2bb62d7952e04c83921e724c9392af4a
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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