Acetic Acid → (S)-3-amino-2-chloro-4-N-(1-methoxymethyl-3-methoxypropyl)-6-methyl-pyridin-4-amine
Reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][CH:12]([CH2:17][O:18][CH3:19])[CH2:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4]([CH3:20])[N:3]=1.C(O)(=O)C>CO.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH3:20])=[CH:5][C:6]=1[NH:11][C@H:12]([CH2:17][O:18][CH3:19])[CH2:13][CH2:14][O:15][CH3:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Chloro-6-methyl-3-nitro-N-(1-methoxymethyl-3-methoxypropyl)pyridin-4-amine (˜16.82 mmol) was heated at reflux with Fe powder (10 g) in methanol (120 mL) in the presence of glacial acetic acid (10 mL) for 2 h. Then the iron was filtered through celite, the celite was washed with methanol(80 mL) and the filtrate was stripped in vacuo. The residue was dissolved in 10% HCl (120 mL) and EtOAc was added (160 mL). The mixture was neutralized with solid NaHCO3 and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4) and stripped in vacuo (4.1 g). NMR(CDCl3)d 6.4 (s, 1H), 5.2-5.35 (br s, 1H), 3.70-3.80 (m, 1H), 3.2-3.8 (m, 6H), 3.38 (s, 3H), 3.33 (s, 3H), 2.42 (s, 3H), 1.8-2.0 (m, 2H).
Workup
- filtrationThen the iron was filtered through celite
- washthe celite was washed with methanol(80 mL)
- dissolutionThe residue was dissolved in 10% HCl (120 mL)
- additionEtOAc was added (160 mL)
- extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
- washThe combined organic extracts were washed with brine (50 mL)
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-3b9126e595994ec9bcf9297937096136
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448261B1
Reaction notes
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