Thiophene → 3-(2-Amino-5-phenoxy-benzylamino)-N-methyl-N-phenyl-propionamide

HRID 1968775Notes

Reaction equation

HRID 1968775 reaction equation
[CH3:1][N:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3](=[O:24])[CH2:4][CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[N+:21]([O-])=O.S1C=CC=C1.[H][H]>[Pd].CO>[NH2:21][C:9]1[CH:10]=[CH:11][C:12]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][C:8]=1[CH2:7][NH:6][CH2:5][CH2:4][C:3]([N:2]([CH3:1])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 58625076N-Methyl-3-(2-nitro-5-phenoxy-benzylamino)-N-phenyl-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 586251533-(2-Amino-5-phenoxy-benzylamino)-N-methyl-N-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-methyl-3-(2-nitro-5-phenoxy-benzylamino)-N-phenyl-propionamide (2 g, 0.0049 mol), 10% palladium on carbon (1 g), and thiophene solution (1 mL) in 150 mL of MeOH was hydrogenated until 3 equivalents of hydrogen were consumed. The reaction mixture was filtered, and the filtrate was concentrated. The resulting residue was purified by column chromatography on a Biotage. The product containing fractions were collected and concentrated to yield a residue.

Workup

  1. customwere consumed
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was purified by column chromatography on a Biotage
  5. additionThe product containing fractions
  6. customwere collected
  7. concentrationconcentrated
  8. customto yield a residue

Sources & evidence

ORD record
ord-e89d293a69c24ff7ae7281487313d55b
Source dataset
uspto-grants-2013_04
Patent number
US08426429B2

Reaction notes

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