p-Toluenesulfonic acid → 2-(2,6-Dimethylpyridin-4-yl)-6-((4-methylpiperazin-1-yl)methyl)quinazolin-4(3H)-one

HRID 591816노트

반응식

HRID 591816 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[CH:5]=[C:4]([CH3:10])[N:3]=1.[NH2:11][C:12]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15].S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:16][C:14](=[O:15])[C:13]3[C:12](=[CH:20][CH:19]=[C:18]([CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[CH:17]=3)[N:11]=2)[CH:5]=[C:4]([CH3:10])[N:3]=1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 27630042,6-Dimethylpyridine-4-carbaldehydeHCID 23665763Sodium BisulfiteHCID 666710512-Amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide

생성물 1

HCID 1359390682-(2,6-Dimethylpyridin-4-yl)-6-((4-methylpiperazin-1-yl)methyl)quinazolin-4(3H)-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
115 °C

실험 절차

To a solution of 2,6-dimethylpyridine-4-carbaldehyde (0.14 g, 1.00 mmol) in N,N-dimethyl acetamide (8 mL) were added 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide (0.25 g, 1.00 mmol), sodium hydrogensulfite (0.18 g, 1.20 mmol), and p-toluenesulfonic acid (0.057 g, 0.30 mmol). The reaction mixture was stirred at 115° C. for 20 hours under nitrogen, then cooled to room temperature. Solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with sat. NaHCO3, water, then brine, and dried over anhydrous sodium sulfate. Solvent was evaporated and the residue was purified by column chromatography (silica gel 230-400 mesh; 2-3% 7 M ammonia in methanol and dichloromethane as eluent) to give the title compound. Yield: 0.035 g (9.6%). MP 229-230° C. 1H NMR (400 MHz, CDCl3): δ 8.30 (br s, 1H), 7.88 (s, 2H), 7.84 (m, 2H), 3.66 (s, 2H), 2.72 (s, 6H), 2.50 (br s, 8H), 2.30 (s, 3H). MS (ES) m/z: 364.17 (M+1), 182.67 (100%).

후처리

  1. temperaturecooled to room temperature
  2. customSolvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with sat. NaHCO3, water
  5. dry with materialbrine, and dried over anhydrous sodium sulfate
  6. customSolvent was evaporated
  7. customthe residue was purified by column chromatography (silica gel 230-400 mesh; 2-3% 7 M ammonia in methanol and dichloromethane as eluent)

출처 및 근거

ORD 기록
ord-1a3fa5b7e02843fda1963e6c74970a13
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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