Acetyl chloride → n-(4-Amino-5-cyano-6-ethylpyridin-2-yl)acetamide

HRID 1364534Notes

Reaction equation

HRID 1364534 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][CH3:11])[N:5]=[C:4]([NH2:12])[CH:3]=1.[C:13](Cl)([CH3:15])=[O:14]>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH2:10][CH3:11])[N:5]=[C:4]([NH:12][C:13](=[O:14])[CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 451224114,6-Diamino-2-ethyl-nicotinonitrile

Product 1

HCID 66920553n-(4-Amino-5-cyano-6-ethylpyridin-2-yl)acetamideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 4,6-diamino nicotinonitrile from Example 101A (35 mg, 0.22 mmol) was dissolved in 0.5 mL of anhydrous pyridine. AcCl was then dropped in until the TLC shows the starting material was completely consumed (appr. 150 μL of AcCl used). Water was then added, the light-yellow precipitate was collected through filtration and dried in vacuum oven to provide the titled compound (30 mg, 68% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.28 (s, 1H), 7.39 (s, 1H), 6.82 (s, 2H), 2.66 (q, J=7.5 Hz, 2H), 2.06 (s, 3H), 1.19 (t, J=7.5 Hz, 3H). MS (ESI) m/e 205 (M+H)+.

Workup

  1. customwas completely consumed (appr. 150 μL of AcCl used)
  2. additionWater was then added
  3. filtrationthe light-yellow precipitate was collected through filtration
  4. customdried in vacuum oven

Sources & evidence

ORD record
ord-af22593d54de447992803a4fa80028ad
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

Loading…