HCID 69291939, compound → HCID 69290262, compound

HRID 1247430Notes

Reaction equation

HRID 1247430 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][C:8]([O:21][CH2:22][CH3:23])([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[F:20])[C:9]([NH2:11])=[O:10])=[C:5]([N+:26]([O-])=O)[CH:4]=1)#[N:2]>C1COCC1.C(O)C.[Pd]>[NH2:26][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:25]=[CH:24][C:6]=1[CH2:7][C:8]([O:21][CH2:22][CH3:23])([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[F:20])[C:9]([NH2:11])=[O:10]

Participants

5

Reactant 1

HCID 69291939HCID 69291939, compound

Product 1

HCID 69290262HCID 69290262, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-(4-cyano-2-nitro-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide in THF (5 ml) and ethanol (15 ml) was added palladium/C (250 mg). After 24 hrs stirring at rt under hydrogen atmosphere the mixture was filtered, and the filtrate was concentrated to leave a light yellow foam. The crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 1:1) to give (RS)-(2-amino-4-cyano-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide (4.45 g) as light yellow foam. MS 358.7 ([M+H]+)

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate was concentrated
  3. customto leave a light yellow foam
  4. customThe crude product was purified by flash chromatography (cyclohexane=>cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-1beaa0c04c804beb9ebe6b570e0d2266
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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