Water → 2-(2-Methylphenyl)-5-[6-(morpholin-4-yl)pyridine-3-yl]methyl-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

HRID 449984노트

반응식

HRID 449984 반응식
Br[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3=[N:19][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])[C:21](=[O:22])[C:11]3=[N:10]2)=[CH:4][CH:3]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:20]1[C:21](=[O:22])[C:11]2=[N:10][N:9]([CH2:8][C:5]3[CH:6]=[N:7][C:2]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:3][CH:4]=3)[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]2=[N:19]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 468966115-[(6-Bromopyridin-3-yl)methyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

생성물 1

HCID 468970112-(2-Methylphenyl)-5-[6-(morpholin-4-yl)pyridine-3-yl]methyl-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

5-[(6-Bromopyridin-3-yl)methyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one [(Example 22), 60 mg, 0.13 mmol] was dissolved in dimethyl sulfoxide (1 mL) and treated with morpholine (35 mg, 0.40 mmol, 3 equiv) and potassium carbonate (19 mg, 0.13 mmol, 1 equiv). The vessel was sealed and placed into an oil bath preheated at 100° C. for 9 hours. The mixture was cooled to ambient temperature, poured into water (5 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed three times with water and once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 94:6; chloroform:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.29 (1H, br s), 7.69-7.59 (3H, m), 7.57-7.51 (2H, m), 7.44 (1H, m), 7.38-7.29 (3H, m), 6.59 (1H, d, J=9.1 Hz), 5.73 (2H, s), 3.79 (4H, m), 3.50 (4H, m), 2.35 (3H, s) ppm; high resolution mass spectrometry (ES+) m/z 453.2038 [(M+H)+; calculated for C26H25N6O2: 453.2034].

후처리

  1. customThe vessel was sealed
  2. customplaced into an oil bath
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. washThe combined organic extracts were washed three times with water
  5. dry with materialonce with brine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 94:6; chloroform:methanol)

출처 및 근거

ORD 기록
ord-d0aaa05f2b874496af47f0bf2e4e8141
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486946B2

반응 노트

불러오는 중…