Triethylamine → Tert-butyl 2-{2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethoxy}ethylcarbamate

HRID 1008028Notes

Reaction equation

HRID 1008028 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[Cl:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20](Cl)[C:19]([CH3:26])=[C:18]([CH3:27])[N:17]=1.C(N(CC)CC)C>CN(C)C=O>[Cl:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[C:19]([CH3:26])=[C:18]([CH3:27])[N:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamateHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 21913714Tert-butyl 2-{2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethoxy}ethylcarbamateYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of tert-butyl 2-(2-aminoethoxy)ethylcarbamate (23.1 g, 113 mmol) in N,N-dimethylformamide (100 mL) was added over a 1 hour period to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (25.02 g, 113 mmol) in N,N-dimethylformamide (400 mL) containing triethylamine (24 mL, 175 mmol). The reaction mixture was allowed to stir at ambient temperature overnight. The N,N-dimethylformamide was removed under reduced pressure. The residue was dissolved in ethyl acetate (500 mL), washed with water (3×100 ml), dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography (450 g of silica gel eluting sequentially with 3/1 hexanes/ethyl acetate (1.2 L), 2/1 hexanes/ethyl acetate (1.2 L), and 1/1 hexanes/ethyl acetate (1 L)) to provide 20.67 g of tert-butyl 2-{2-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]ethoxy}ethylcarbamate.

Workup

  1. customThe N,N-dimethylformamide was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  3. washwashed with water (3×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (450 g of silica gel eluting sequentially with 3/1 hexanes/ethyl acetate (1.2 L), 2/1 hexanes/ethyl acetate (1.2 L), and 1/1 hexanes/ethyl acetate (1 L))

Sources & evidence

ORD record
ord-f27e363905f5494ab2d8cc5765f6a6d9
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

Loading…