4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide → 4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide

HRID 491874Notes

Reaction equation

HRID 491874 reaction equation
[CH:1]1([CH:7]([NH:22][CH2:23][C:24]2[C:29]([N+:30]([O-])=O)=[CH:28][N:27]=[C:26]([O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:25]=2)[CH2:8][CH2:9][C:10]([N:12]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][CH2:14][OH:15])=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:30][C:29]1[C:24]([CH2:23][NH:22][CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9][C:10]([N:12]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:13][CH2:14][OH:15])=[O:11])=[CH:25][C:26]([O:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[N:27][CH:28]=1

Participants

4

Reactant 1

HCID 670236094,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide

Product 1

HCID 670234544-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide (0.1 g, 0.18 mmol) in MeOH (10 mL) was added a catalytic amount of Pd—C (10% on activated carbon) under N2, and the reaction mixture was subjected to hydrogenation under 5 psi for one hour. The catalyst was filtered out, and the MeOH was evaporated to yield a residue which was purified by preparative TLC (100% EtOAc) to yield 4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4,N-dicyclohexyl-N-(2-hydroxy-ethyl)-butyramide as an oil.

Workup

  1. filtrationThe catalyst was filtered out
  2. customthe MeOH was evaporated
  3. customto yield a residue which
  4. customwas purified by preparative TLC (100% EtOAc)

Sources & evidence

ORD record
ord-fa8bd1c87fdd48d683cef2511559b946
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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