Ethanol → 2-[(5-Amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-3,N-dimethyl-N-phenethyl-butyramide

HRID 491917Notes

Reaction equation

HRID 491917 reaction equation
[CH3:1][CH:2]([CH3:34])[CH:3]([NH:16][CH2:17][C:18]1[C:23]([N+:24]([O-])=O)=[CH:22][N:21]=[C:20]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:19]=1)[C:4]([N:6]([CH3:15])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].C(O)C>[Pd].C(OCC)(=O)C>[NH2:24][C:23]1[C:18]([CH2:17][NH:16][CH:3]([CH:2]([CH3:34])[CH3:1])[C:4]([N:6]([CH3:15])[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])=[CH:19][C:20]([O:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:21][CH:22]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 670236673,N-Dimethyl-2-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-phenethyl-butyramide

Product 1

HCID 670236882-[(5-Amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-3,N-dimethyl-N-phenethyl-butyramide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,N-dimethyl-2-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-phenethyl-butyramide (2.1 g, 1.38 mmol), 10% Pd on carbon (2 g), ethanol (75 mL) and ethyl acetate (75 mL) were shaken under a hydrogen atmosphere (50 psi). After 2 hours, the hydrogen was evacuated and the bottle was purged with nitrogen. The resulting mixture was filtered through glass fiber filter paper and the solvent evaporated under low pressure to yield a solid.

Workup

  1. customthe hydrogen was evacuated
  2. customthe bottle was purged with nitrogen
  3. filtrationThe resulting mixture was filtered through glass fiber
  4. filtrationfilter paper
  5. customthe solvent evaporated under low pressure
  6. customto yield a solid

Sources & evidence

ORD record
ord-b05a5b80daea44fda9204fffbd105cb7
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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