Triethylamine → (R)-N6-(2,4-Dimethoxybenzyl)-3-nitro-N2-(1-(pyridin-3-yl)ethyl)pyridine-2,6-diamine

HRID 1363143Notes

Reaction equation

HRID 1363143 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C@H:25]([NH2:27])[CH3:26])[CH:20]=1.[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33]>C(OCC)(=O)C>[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH:33][C:4]1[N:3]=[C:2]([NH:27][C@@H:25]([C:21]2[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=2)[CH3:26])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 5972502,4-DimethoxybenzylamineHCID 1084920(R)-1-(Pyridin-3-yl)ethanamine

Product 1

HCID 59727023(R)-N6-(2,4-Dimethoxybenzyl)-3-nitro-N2-(1-(pyridin-3-yl)ethyl)pyridine-2,6-diamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,6-dichloro-5-nitropyridine (46) (0.5 g) in THE (20 mL) was cooled to 0° C. and treated with 1.6 mL triethylamine followed by (R)-1-pyridin-3-yl-ethylamine (300 μL). The mixture was stirred for 1.5 h, then warmed to RT and stirred another 20 h. 2,4-Dimethoxybenzylamine (0.8 mL) was added and the mixture was heated at 50° C. for four hours. The mixture was diluted with ethyl acetate and washed twice with saturated sodium chloride solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (50→100% ethyl acetate in hexanes) provided 761 mg of (R)—N6-(2,4-Dimethoxybenzyl)-3-nitro-N2-(1-(pyridin-3-yl)ethyl)pyridine-2,6-diamine (64).

Workup

  1. stirringstirred another 20 h
  2. temperaturethe mixture was heated at 50° C. for four hours
  3. washwashed twice with saturated sodium chloride solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-46807e7ce22a4939aef767ee70d03932
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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