Ethanol → HCID 69778171, compound

HRID 1760669Notes

Reaction equation

HRID 1760669 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11](C)[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].[CH2:27](O)C>[Pd]>[CH3:23][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[O:14][C:9]1[C:8]([NH2:24])=[C:7]([NH:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:12]([CH3:27])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 21912047HCID 21912047, compound

Product 1

HCID 69778171HCID 69778171, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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 IC 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 Ute 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), 1.451.75 (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

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe mixture was filtered through Celite™
  3. concentrationthe filtrate was concentrated to dryness
  4. customto give a purple glass form (810 mg) which
  5. customwas purified through silica gel column chromatography

Sources & evidence

ORD record
ord-0025b3138b8644a3a6f05c3e1bbf85a5
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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