Triethylamine → HCID 58319377, compound

HRID 444699Notes

Reaction equation

HRID 444699 reaction equation
Cl[C:2]([C:11]1[S:12][CH:13]=[C:14]([CH3:17])[C:15]=1[Cl:16])=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[CH3:19][NH:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23].C(N(CC)CC)C>C(#N)C>[Cl:16][C:15]1[C:14]([CH3:17])=[CH:13][S:12][C:11]=1/[C:2](/[NH:23][C@H:22]([CH3:24])[C:21]([NH:20][CH3:19])=[O:25])=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 76759590HCID 76759590, compound

Product 1

HCID 58319377HCID 58319377, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (0.351 g, 1.21 mmol, 1 eq.) in 3 ml of acetonitrile was added N-methyl-L-alaninamide hydrochloride (0.201 g, 1.45 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.490 g, 4.84 mmol, 4 eq.). The reaction was microwaved (130° C., 300 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 ethyl (2Z)-3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]amino}acrylate (0.26 g, 57% yield) as a mixture of atropoisomers.

Workup

  1. customThe reaction was microwaved
  2. custom(130° C., 300 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-c07b7fe3a21c4708944482a536cc5258
Source dataset
uspto-grants-2013_07
Patent number
US08476197B2

Reaction notes

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