Benzyl[3-(aminocarbonyl)-5-(2,4-difluorophenyl)-2-thienyl]carbamate → 2-Amino-5-(2,4-difluorophenyl)thiophene-3-carboxamide

HRID 385696Notes

Reaction equation

HRID 385696 reaction equation
C(OC(=O)[NH:10][C:11]1[S:12][C:13]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[NH2:10][C:11]1[S:12][C:13]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17]

Participants

5

Reactant 2

HCID 59526381Benzyl[3-(aminocarbonyl)-5-(2,4-difluorophenyl)-2-thienyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 595262952-Amino-5-(2,4-difluorophenyl)thiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of benzyl[3-(aminocarbonyl)-5-(2,4-difluorophenyl)-2-thienyl]carbamate (240 mg, 0.618 mmol) and 10% palladium on carbon (326 mg, 0.306 mmol) in ethanol (130 mL) was placed under a hydrogen atmosphere by performing 5×15 second vacuum/hydrogen purge (supplied by balloon) fill cycles while vigorously stirring the mixture. The reaction was heated to reflux for 18 hours and then allowed to cool to ambient temperature. The suspension was filtered; the filtrate was collected and concentrated to yield the title compound as a light yellow solid.

Workup

  1. custompurge (supplied by balloon) fill cycles
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 18 hours
  4. filtrationThe suspension was filtered
  5. customthe filtrate was collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95a6580003ba427292fd01887558f7da
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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