Morpholine → HCID 59507540, 화합물

HRID 1043804

반응식

HRID 1043804 반응식
Br[C:2]1[N:7]=[C:6](Br)[CH:5]=[C:4]([Br:9])[N:3]=1.[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]([NH2:20])[CH:11]=1.CCN(C(C)C)C(C)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(#N)C>[Br:9][C:4]1[N:3]=[C:2]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:7]=[C:6]([NH:20][C:12]2[CH:11]=[N:10][C:19]3[C:14]([CH:13]=2)=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:5]=1

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 113753-AminoquinolineHCID 81531DiisopropylethylamineHCID 2585802,4,6-Tribromopyrimidine

생성물 1

HCID 59507540HCID 59507540, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
45 °C

실험 절차

To a solution of 2,4,6-tribromopyrimidine (5.40 g, 17.2 mmol) in acetonitrile (60 mL) was added quinolin-3-amine, followed by DIEA (8.99 mL, 51.6 mmol). The reaction mixture was heated to 45° C. overnight. Morpholine (1.50 mL, 17.2 mmol) was then added, and the reaction mixture continued heating for 4 h. The reaction mixture was then cooled to room temperature, concentrated and dissolved in EtOAc (about 500 mL), the organic solution was washed with saturated NaHCO3 (3×), H2O (2×), brine (1×) and dried over Na2SO4. The solution was then evaporated in the presence of silica gel and purified by column chromatography (SiO2, 15-25% EtOAc/Hexanes) to yield N-(6-bromo-2-morpholinopyrimidin-4-yl)quinolin-3-amine. LC/MS (m/z): 386.1 (MH+).

후처리

  1. temperaturethe reaction mixture continued heating for 4 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated
  4. dissolutiondissolved in EtOAc (about 500 mL)
  5. washthe organic solution was washed with saturated NaHCO3 (3×), H2O (2×), brine (1×)
  6. dry with materialdried over Na2SO4
  7. customThe solution was then evaporated in the presence of silica gel
  8. custompurified by column chromatography (SiO2, 15-25% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-a424ee4c58394739ba3f92415541aba8
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563549B2

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