1-Ethyl-propyl[6-methyl-3-nitro-2-(4-chloro-2,6-dimethyl-phenoxy)-pyridin-4-yl]-amine → 2-(2,6-Dimethyl-phenoxy)-N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine
Reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18](Cl)=[CH:17][C:16]=2[CH3:23])[C:8]=1[N+:24]([O-])=O)[CH2:4][CH3:5])[CH3:2]>C(O)C.[Pd]>[CH3:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:23])[C:15]=1[O:14][C:9]1[C:8]([NH2:24])=[C:7]([NH:6][CH:3]([CH2:1][CH3:2])[CH2:4][CH3:5])[CH:12]=[C:11]([CH3:13])[N:10]=1Participants
Procedure
A mixture of (1-ethyl-propyl)-[6-methyl-3-nitro-2-(4-chloro-2,6-dimethyl-phenoxy)-pyridin-4-yl]-amine (800 mg, 2.12 mmol) and 160 mg of 10% Pd/C in 150 ml of ethanol was hydrogenated at 50 psi overnight. The mixture was filtered through Celite™ and the filtrate was concentrated to dryness to give a purple glass form (810 mg) which was purified through silica gel column chromatography using 1:1 chloroform:hexane as eluent to give the title compound as tan crystals (360 mg), mp 98-100° C. 1H NMR (CDCl3) δ 7.05 (m, 3H), 6.11 (s, 1H), 4.00 (brs, 1H), 3.28 (m, 1H), 3.09 (brs, 2H), 2.14 (s, 9H), 1.45-1.75 (m, 4H), 0.98 (t, 6H) ppm. The corresponding HCl salt was prepared as white solid, mp 158-162° C., 1H NMR (D2O) δ 7.27 (s, 3H), 6.67 (s, 1H), 3.65 (m, 1H), 2.27 (s, 3H), 2.16 (s, 6H), 1.45-1.80 (m, 4H), 0.93 (t, 6H) ppm.
Workup
- customwas hydrogenated at 50 psi overnight
- filtrationThe mixture was filtered through Celite™
- concentrationthe filtrate was concentrated to dryness
- customto give a purple glass form (810 mg) which
- customwas purified through silica gel column chromatography
Sources & evidence
- ORD record
- ord-62388ca05c0a4afc8311cc521f36ea3f
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06956047B1
Reaction notes
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