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3-Cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamide → 3-[(5-Amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

HRID 491913
Notes
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Reaction equation

HRID 491913 reaction equation
[CH:1]1([CH:7]([NH:18][CH2:19][C:20]2[C:25]([N+:26]([O-])=O)=[CH:24][N:23]=[C:22]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:21]=2)[CH2:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:26][C:25]1[C:20]([CH2:19][NH:18][CH:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:10])=[CH:21][C:22]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:23][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 670235503-Cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamideHCID 178418361HCID 178418361, compound

Product 1

HCID 670236173-[(5-Amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst
HCID 702
Ethanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

In a Parr bottle 10% Pd/C (0.42 g) was added and cooled to −78° C., then a solution of 3-cyclohexyl-N-(3,3-dimethyl-butyl)-3-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-propionamide (0.42 g, 0.87 mmol) in ethyl acetate (5 mL) and ethanol (20 mL) was added. The resulting mixture was subjected to hydrogen atmosphere and shaken for 3.5 h. The hydrogen was purged with nitrogen, then the reaction mixture was filtered (glass fiber filter paper) and the solvent was evaporated under reduced pressure to yield the title compound as a residue.

Workup

  1. customThe hydrogen was purged with nitrogen
  2. filtrationthe reaction mixture was filtered
  3. filtration(glass fiber filter paper)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-682d19bdc14149e88f2897dd0fd55aad
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07531545B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes