p-Toluenesulfonic acid → 3-(4-sec-butylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4(3H)-one

HRID 1846336노트

반응식

HRID 1846336 반응식
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:27][C:28]1[CH:46]=[CH:45][CH:44]=[CH:43][C:29]=1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]([CH2:41][CH3:42])[CH3:40])=[CH:35][CH:34]=1)=[O:31]>CC(N(C)C)=O>[CH:39]([C:36]1[CH:37]=[CH:38][C:33]([N:32]2[C:30](=[O:31])[C:29]3[C:28](=[CH:46][CH:45]=[CH:44][CH:43]=3)[N:27]=[C:9]2[C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:34][CH:35]=1)([CH2:41][CH3:42])[CH3:40]

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 167700372-Amino-N-(4-sec-butylphenyl)benzamideHCID 23665763Sodium Bisulfite

생성물 1

HCID 468414133-(4-sec-butylphenyl)-2-(6-methoxypyridin-3-yl)quinazolin-4(3H)-one수율 26%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
150 °C

실험 절차

6-Methoxy-3-pyridinecarboxaldehyde (1.20 mmol), NaHSO3 (0.200 g, 1.90 mmol) and p-TsOH (0.024 g, 0.12 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.340 g, 1.20 mmol) in DMA (10 mL). The mixture was heated and stirred at 150° C. overnight and concentrated in vacuo. The residue was dissolved in EtOAc, and washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 15% to 100% EtOAc in heptane, afforded the title compound as a white solid (26%). 1H-NMR (300 MHz, DMSO-d6): δ 8.11-8.27 (m, 2H), 7.89-7.91 (m, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.51-7.67 (m, 2H), 7.11-7.33 (m, 4H), 6.62 (d, J=8.0 Hz, 1H), 3.77 (s, 3H), 2.54-2.68 (m, 1H), 1.30-1.71 (m, 2H), 1.16 (d, J=7.0 Hz, 3H), 0.64 (t, J=7.4 Hz, 3H). MS (APCI) m/z: 386 (M+H)+.

후처리

  1. temperatureThe mixture was heated
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with H2O
  5. dry with materialbrine, dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 15% to 100% EtOAc in heptane

출처 및 근거

ORD 기록
ord-59d627152e774058b7abf294dba2b145
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

반응 노트

불러오는 중…