Thiophene → 3-(2-Amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide

HRID 390196Notes

Reaction equation

HRID 390196 reaction equation
[C:1]([C:9]1[CH:10]=[CH:11][C:12]([N+:29]([O-])=O)=[C:13]([CH:28]=1)[CH2:14][NH:15][CH2:16][CH2:17][C:18]([N:20]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH3:21])=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S1C=CC=C1.[H][H]>[Pd].CO>[NH2:29][C:12]1[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:28][C:13]=1[CH2:14][NH:15][CH2:16][CH2:17][C:18]([N:20]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)[CH3:21])=[O:19]

Participants

6

Reactant 3

HCID 8030ThiopheneHCID 177564853-(5-Benzoyl-2-nitro-benzylamino)-N-cyclohexyl-N-methyl-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 586251113-(2-Amino-5-benzoyl-benzylamino)-N-cyclohexyl-N-methyl-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(5-benzoyl-2-nitro-benzylamino)-N-cyclohexyl-N-methyl-propionamide (9 g, 0.02 mol), 10% palladium on carbon (2 g), and thiophene solution (2 mL) in MeOH (250 mL) was hydrogenated until 3 equivalents of hydrogen were consumed. The reaction mixture was filtered through Dicalite, and the filtrate was concentrated to yield a residue.

Workup

  1. customwere consumed
  2. filtrationThe reaction mixture was filtered through Dicalite
  3. concentrationthe filtrate was concentrated
  4. customto yield a residue

Sources & evidence

ORD record
ord-6f61c0efea5d46b7bb36b922e988d401
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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