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

HRID 1846336ノート

反応式

HRID 1846336 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-59d627152e774058b7abf294dba2b145
出典データセット
uspto-grants-2015_02
特許番号
US08952021B2

反応ノート

読み込み中…