Triethylamine → N-cyclopropyl-4-methyl-3-(2-(6-(2-morpholinoethylamino)pyridin-3-yl)ethynyl)benzamide

HRID 1042637ノート

反応式

HRID 1042637 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:7][CH:8]=1)#[CH:2].[CH:18]1([NH:21][C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25](I)[CH:24]=2)[CH2:20][CH2:19]1.C(N(CC)CC)C>O1CCOCC1.CCOC(C)=O.[Cu]I>[CH:18]1([NH:21][C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([C:2]#[C:1][C:3]3[CH:8]=[N:7][C:6]([NH:9][CH2:10][CH2:11][N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)=[CH:5][CH:4]=3)[CH:24]=2)[CH2:19][CH2:20]1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamideHCID 594279395-ethynyl-N-(2-morpholinoethyl)pyridin-2-amine

生成物 1

HCID 59427921N-cyclopropyl-4-methyl-3-(2-(6-(2-morpholinoethylamino)pyridin-3-yl)ethynyl)benzamide

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

5-Ethynyl-N-(2-morpholinoethyl)pyridin-2-amine (0.54 g, 2.36 mmol), N-cyclopropyl-3-iodo-4-methylbenzamide (0.71 g, 2.36 mmol), and triethylamine (0.49 mL, 3.54 mmol) were dissolved in dioxane (10 mL) before these were sparged with nitrogen for 15 min.; palladium dichloro-bis-triphenylphosphine (83 mg, 0.12 mmol) and copper (I) iodide (45 mg, 0.24 mmol) were added before the reaction mixture was heated to 90° C. for 6 h. The reaction mixture was diluted with 100 mL EtOAc, washed with 50 mL saturated, aqueous NaHCO3, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a yellow oil. MS (ES+): 406 (M+H)−.

後処理

  1. customthese were sparged with nitrogen for 15 min.
  2. washwashed with 50 mL saturated
  3. dry with materialaqueous NaHCO3, and dried over anhydrous Na2SO4
  4. customAfter purification by chromatography

出典と根拠

ORDレコード
ord-4560e2f82b3845d4b4c2d2407a6313d3
出典データセット
uspto-grants-2013_10
特許番号
US08557996B2

反応ノート

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