Triethylamine → HCID 58319377、化合物

HRID 444699ノート

反応式

HRID 444699 の反応式
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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 76759590HCID 76759590、化合物

生成物 1

HCID 58319377HCID 58319377、化合物収率 60.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c07b7fe3a21c4708944482a536cc5258
出典データセット
uspto-grants-2013_07
特許番号
US08476197B2

反応ノート

読み込み中…