2-(4-ethoxyphenyl)acetyl Chloride → 5-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide

HRID 1796520Notes

Reaction equation

HRID 1796520 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13])[CH:5]=[N:6][C:7]=1[NH:8][CH2:9][CH:10]=[CH2:11].[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[O:30])=[CH:24][CH:23]=1)[CH3:20]>ClCCl>[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([NH:1][C:2]2[CH:3]=[C:4]([C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13])[CH:5]=[N:6][C:7]=2[NH:8][CH2:9][CH:10]=[CH2:11])=[O:30])=[CH:24][CH:23]=1)[CH3:20]

Participants

4

Reactant 2

HCID 116297822-(4-ethoxyphenyl)acetyl ChlorideHCID 221813075-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide

Product 1

HCID 221813495-[[(4-ethoxyphenyl)acetyl]amino]-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamideYield 2,585.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide (1.61 g, 6.50 mmol) in dichloromethane (50 mL) at 0° C. was added 4-ethoxy-benzeneacetyl chloride (1.35 g, 6.80 mmol). The mixture was stirred for 3 hours at room temperature. The reaction was then quenched with NaHCO3 saturated aqueous solution (100 mL) and extracted with dichloromethane (50 mL). The aqueous phase was back-extracted with additional dichloromethane (2×50 mL). The organic phases were combined, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified using silica gel flash chromatography ([2% MeOH+0.5% NH4OH aq] in CH2Cl2) to provide 1:69 g of the title compound 5-[[(4-ethoxyphenyl)acetyl]amino]-NN-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide (63.3% yield from 5-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide). 1H-NMR (400 MHz, CDCl3): δ 1.18 (t,J=7.2 Hz, 6H), 1.41 (t,J=7.8 Hz, 3H), 3.42 (br s, 1H), 3.69 (s, 2H), 4.02 (m, 8H), 5.13 (m, 2H), 5.92 (m, 1 H), 6.90 (m, 2H), 7.27 (m, 2H), 7.34 (m, 1H), 8.00 (m, 1H). MS (ES) (M+H)+: 411.

Workup

  1. customThe reaction was then quenched with NaHCO3 saturated aqueous solution (100 mL)
  2. extractionextracted with dichloromethane (50 mL)
  3. extractionThe aqueous phase was back-extracted with additional dichloromethane (2×50 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. customto provide 1

Sources & evidence

ORD record
ord-1aa1b58075a34c5a9be41a7111c5b7bb
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

Loading…