Triethylamine → N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide

HRID 37837Notes

Reaction equation

HRID 37837 reaction equation
[CH3:1][N:2]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5](Cl)=[O:6].C(N(CC)CC)C.[CH3:24][C:25]1[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([NH:32][CH3:33])[CH:26]=1>ClCCl>[CH3:24][C:25]1[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([N:32]([CH3:33])[C:5](=[O:6])[CH2:4][CH2:3][N:2]([CH3:1])[C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3792909N,4,6-trimethylpyridin-2-amineHCID 86649694HCID 86649694, compound

Product 1

HCID 66851224N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamideYield 43.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[methyl-(4-nitro-phenyl)-amino]-propionyl chloride (550 mg, 4.04 mmol) in dichloromethane (5 mL) was cooled to 0° C., triethylamine (1.12 mL, 8.08 mmol) was added followed, after 5 min, by (4,6-dimethyl-pyridin-2-yl)-methyl-amine (1.14 g, 4.73 mmol). The reaction mixture was warmed to room temperature and stirred for 30 min then partitioned between water and dichloromethane. The organic phase was separated, washed with saturated bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue which was purified by column chromatography over silica gel (60-120 mesh) using 20% ethyl acetate in hexane as eluent to afford N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide (600 mg, 43%) as a yellow solid.

Workup

  1. customthen partitioned between water and dichloromethane
  2. customThe organic phase was separated
  3. washwashed with saturated bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue which
  7. customwas purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-89189791ab6349a7b012f1d22fbf000c
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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