Triethylamine → ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-[(3-methyl-2-phenylbutyl)amino]acrylate

HRID 444696Notes

Reaction equation

HRID 444696 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.[C:19]1([CH:25]([CH:28]([CH3:30])[CH3:29])[CH2:26][NH2:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C>[Cl:17][C:12]1[C:11](/[C:2](/[NH:27][CH2:26][CH:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:28]([CH3:30])[CH3:29])=[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 671156282-Phenyl-3-methylbutylamine hydrochlorideHCID 86654759Ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate

Product 1

HCID 58319381ethyl (2Z)-3-(2-chloropyridin-3-yl)-2-cyano-3-[(3-methyl-2-phenylbutyl)amino]acrylateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.2 g, 0.738 mmol, 1 eq.) in 3 ml of acetonitril was added 2-phenyl-3-methylbutylamine hydrochloride (0.147 g, 0.738 mmol, 1 eq.) at room temperature followed by triethylamine (TEA) (0.164 g, 1.62 mmol, 2.2 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)-2-cyano-3-[(3-methyl-2-phenylbutyl)amino]acrylate (0.253 g, 85% 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-a27329f6580448479a869dffb4b96c46
Source dataset
uspto-grants-2013_07
Patent number
US08476197B2

Reaction notes

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