Diisopropylethylamine → (4-(6-Amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5-ylamino)phenyl)(morpholino)methanone

HRID 445919노트

반응식

HRID 445919 반응식
Cl[C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH3:18])[N:5]=[N:6][C:7]=1[NH2:8].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[NH2:8][C:7]1[N:6]=[N:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH3:18])=[N:3][C:2]=1[NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[O:27])=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5778154-(Morpholine-4-carbonyl)anilineHCID 582795485-Chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine

생성물 1

HCID 58279511(4-(6-Amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5-ylamino)phenyl)(morpholino)methanone수율 33.9%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (1.05 g, 3.95 mmol), (4-aminophenyl)(morpholino)methanone (1.630 g, 7.90 mmol), and N,N-diisopropylethylamine (1.243 mL, 7.11 mmol) in 1,4-dioxane (60 mL) was heated at reflux for 2 days. The volatiles were removed under vacuum. To the residue was added water (60 mL). The precipitating material was collected by suction filtration. The filter cake was purified by ISCO (120 g silica gel, solid loading, 3-8% MeOH/CH2Cl2) to provide the desired product, (4-(6-amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5-ylamino)phenyl)(morpholino)methanone (0.595 g, 1.339 mmol, 33.9% yield), as a yellow solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customThe volatiles were removed under vacuum
  4. additionTo the residue was added water (60 mL)
  5. filtrationThe precipitating material was collected by suction filtration
  6. customThe filter cake was purified by ISCO (120 g silica gel, solid loading, 3-8% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-c5739192b8854b41a2239b479b0afb0b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476430B2

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