Triethylamine → (2,2-Dimethyl-propylamino)-pyridin-3-yl-acetic acid ethyl ester

HRID 352216

Reaction equation

HRID 352216 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5](Br)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].[CH2:14]([NH2:19])[C:15]([CH3:18])([CH3:17])[CH3:16].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([NH:19][CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79882NeopentylamineHCID 21985933Ethyl 2-bromo-2-(pyridin-3-yl)acetate

Product 1

HCID 69848432(2,2-Dimethyl-propylamino)-pyridin-3-yl-acetic acid ethyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromopyridin-3-yl-acetic acid ethyl ester (2.54 g; 10.2 mmol), prepared in a manner similar to preparation 340, was reacted in refluxing CH2Cl2, overnight with neopentylamine (4.83 mL; 41.0 mmol; 4 equiv) and Et3N (5.8 mL; 41.0 mmol; 4 equiv). The reaction solution was evaporated to dryness, dissolved in CH2Cl2, washed five times with saturated NaHCO3(aq), washed once with saturated NaCl (aq), dried with Na2SO4, filtered, and concentrated in vacuo. The resulting brown oil was purified with silica gel chromatography in a 3×25 cm glass column using a 0.5% methanol/chloroform (v/v) mobile phase. A second column purification with 100% chloroform followed by 1% methanol/chloroform (v/v) produced pure product as a yellow oil (1.0 g; 40% yield).

Workup

  1. customwas reacted
  2. customThe reaction solution was evaporated to dryness
  3. dissolutiondissolved in CH2Cl2
  4. washwashed five times with saturated NaHCO3(aq)
  5. washwashed once with saturated NaCl (aq)
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting brown oil was purified with silica gel chromatography in a 3×25 cm glass column
  10. customA second column purification with 100% chloroform

Sources & evidence

ORD record
ord-8cd34e559d1e4564a2e3182ef4e88415
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Linked notes

Loading…