(S)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl ester → (S)-3-(3-Amino-6-methyl-pyridin-2-ylamino)-hexanoic acid ethyl ester

HRID 2175163Notes

Reaction equation

HRID 2175163 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C@@H:6]([NH:10][C:11]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[C:13]([CH3:20])[N:12]=1)[CH2:7][CH2:8][CH3:9])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C@@H:6]([NH:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([CH3:20])[N:12]=1)[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 58497448(S)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl ester

Product 1

HCID 58497432(S)-3-(3-Amino-6-methyl-pyridin-2-ylamino)-hexanoic acid ethyl esterYield 109%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a slurry of (S)-3-(6-methyl-3-nitro-pyridin-2-ylamino)-hexanoic acid ethyl ester (358 mg, 1.21 mmol) in MeOH (10 mL) was added Pd/C (150 mg). The reaction mixture was de-gassed using house vacuum and saturated with H2. The reaction mixture was stirred at room temperature for 3 hours. The mixture was filtered through a celite and the filtrate was concentrated to afford 350 mg (100%) of the desired product as pale yellow oil. The resulting residue was used for the next reaction without further purification.

Workup

  1. customThe reaction mixture was de-gassed
  2. filtrationThe mixture was filtered through a celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3ea53094c76b489a8c9a758bbfdc1aaf
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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