Acetyl chloride → Ethyl 2-(6-acetamidopyridin-2-yl)acetate

HRID 572922Notes

Reaction equation

HRID 572922 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([NH:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][CH:3]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 13060163Ethyl (6-aminopyridin-2-yl)acetate

Product 1

HCID 86719105Ethyl 2-(6-acetamidopyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of ethyl 2-(6-aminopyridin-2-yl)acetate (50 mg, 0.28 mmol) and N-ethyl-N-isopropylpropan-2-amine (71.0 mg, 0.55 mmol) in DCM was added acetyl chloride (43.2 mg, 0.55 mmol) dropwise at room temperature. The mixture was continued to stir for 1 h, washed with brine and evaporated in vacuum to dryness. The residue was purified by a standard method to afford desired compound. LC-MS: m/z (M+H)=222.4

Workup

  1. washwashed with brine
  2. customevaporated in vacuum to dryness
  3. customThe residue was purified by a standard method

Sources & evidence

ORD record
ord-fec39a3f76a84451b28cb2b240e68729
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

Loading…