Triethylamine → ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate

HRID 444697ノート

反応式

HRID 444697 の反応式
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.[Cl:19][C:20]1[C:21]([CH2:30][CH2:31][NH2:32])=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1.C(N(CC)CC)C>O1CCCC1>[Cl:17][C:12]1[C:11](/[C:2](/[NH:32][CH2:31][CH2:30][C:21]2[C:20]([Cl:19])=[CH:25][C:24]([C:26]([F:29])([F:28])[F:27])=[CH:23][N:22]=2)=[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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 669124442-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)ethan-1-amine hydrochlorideHCID 86654759Ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate

生成物 1

HCID 58319376ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate収率 100.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of ethyl 3-chloro-3-(2-chloropyridin-3-yl)-2-cyanoacrylate (0.1 g, 0.369 mmol, 1 eq.) in 5 ml of tetrahydrofuran were added 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethanamine hydrochloride (0.106 g, 0.40 mmol, 1.1 eq.) and triethylamine (TEA) (0.112 g, 1.10 mmol, 3 eq.) at room temperature. After being stirred for 8 h at 80° C., the mixture was evaporated. The residue was diluted with AcOEt and the precipitate was filtered off. The filtrate was evaporated and the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(2-chloropyridin-3-yl)-3-({2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}amino)-2-cyanoacrylate (0.170 g, 99% yield).

後処理

  1. customthe mixture was evaporated
  2. additionThe residue was diluted with AcOEt
  3. filtrationthe precipitate was filtered off
  4. customThe filtrate was evaporated

出典と根拠

ORDレコード
ord-4e641171f47a466598a9bbece19d4268
出典データセット
uspto-grants-2013_07
特許番号
US08476197B2

反応ノート

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