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

HRID 1042637노트

반응식

HRID 1042637 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-4560e2f82b3845d4b4c2d2407a6313d3
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557996B2

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