(R)-3-(2-Chloro-6-methyl-3-nitro-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl ester → (R)-3-(5-Amino-2-methyl-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175172Notes

Reaction equation

HRID 2175172 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C@@H:6]([NH:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16](Cl)[C:15]=1[N+:22]([O-])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C@@H:6]([NH:13][C:14]1[C:15]([NH2:22])=[CH:16][N:17]=[C:18]([CH3:20])[CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 58497456(R)-3-(2-Chloro-6-methyl-3-nitro-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497452(R)-3-(5-Amino-2-methyl-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl esterYield 110.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of (R)-3-(2-chloro-6-methyl-3-nitro-pyridin-4-ylamino)-3-phenyl-propionic acid ethyl ester (650 mg, 1.79 mmol) in MeOH (20 ml) was added slurry of Pd/C (500 mg) in MeOH (2 mL). The reaction mixture was degassed using house vacuum. The flask was saturated with H2 and stirred under a H2 balloon for 3 hours. When the reaction was complete, the mixture was filtered through a pad of celite and the filtrate was concentrated to afford 590 mg (100%) of the title compound. The resulting light brown oily residue was used for the next reaction without further purification. LCMS, M++1, m/z: 300.92.

Workup

  1. customThe reaction mixture was degassed
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f1ce9fa585e0437c821ab77025a9c108
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

Loading…