Triethylamine → 3-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile

HRID 444705Notes

Reaction equation

HRID 444705 reaction equation
Cl[C:2]([C:6]1[C:7]([Cl:12])=[N:8][CH:9]=[CH:10][CH:11]=1)=[CH:3][C:4]#[N:5].Cl.[CH2:14]([CH:16]1[CH2:18][CH:17]1[NH2:19])[CH3:15].C(N(CC)CC)C>C(#N)C>[Cl:12][C:7]1[C:6]([C:2]([NH:19][CH:17]2[CH2:18][CH:16]2[CH2:14][CH3:15])=[CH:3][C:4]#[N:5])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 129536982-Ethylcyclopropan-1-amine hydrochlorideHCID 767595933-Chloro-3-(2-chloropyridin-3-yl)acrylonitrile

Product 1

HCID 767595953-(2-Chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrileYield 57.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-3-(2-chloropyridin-3-yl)acrylonitrile (1.4 g, 7.03 mmol, 1 eq.) in 15 ml of acetonitrile was added 2-ethylcyclopropanamine hydrochloride (1.02 g, 8.44 mmol, 1.2 eq.) followed by triethylamine (TEA) (1.06 g, 10.55 mmol, 1.5 eq.). The reaction was microwaved (130° C., 2000 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give 3-(2-chloropyridin-3-yl)-3-[(2-ethylcyclopropyl)amino]acrylonitrile (0.998 g, 51% yield).

Workup

  1. customThe reaction was microwaved
  2. custom(130° C., 2000 s, fixed hold, high absorption)
  3. customthe solvent evaporated
  4. customThe residual oil was triturated in ethyl acetate
  5. customthe white solid removed by filtration
  6. concentrationAfter concentration under vacuum

Sources & evidence

ORD record
ord-1c51fc11b8234b18ba30d39a2625396c
Source dataset
uspto-grants-2013_07
Patent number
US08476197B2

Reaction notes

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