Triethylamine → HCID 58319375, compound

HRID 444698Notes

Reaction equation

HRID 444698 reaction equation
Cl[C:2]([C:11]1[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=1)=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl:18][C:19]1[N:24]=[CH:23][C:22]([CH:25]([NH2:27])[CH3:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C>[Cl:17][C:12]1[C:11](/[C:2](/[NH:27][CH:25]([C:22]2[CH:23]=[N:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH3:26])=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 157456051-(6-Chloropyridin-3-yl)ethan-1-amineHCID 86654759Ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate

Product 1

HCID 58319375HCID 58319375, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-chlor-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.150 g, 0.55 mmol, 1 eq.) in 3 ml of acetonitrile was added 1-(6-chloropyridin-3-yl)ethanamine (0.103 g, 0.66 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.167 g, 1.66 mmol, 3 eq.). The reaction was microwaved (130° C., 600 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-{[1-(6-chloropyridin-3-yl)ethyl]amino}-2-cyanoacrylate (0.157 g, 68% yield) as a mixture of 2 atropoisomers.

Workup

  1. customThe reaction was microwaved
  2. custom(130° C., 600 s, fixed hold, high absorption)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-ba6fcd13e4a14af2b8cadfafb7e4f3b0
Source dataset
uspto-grants-2013_07
Patent number
US08476197B2

Reaction notes

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