2-Fluoro-5-formylpyridine → 3-(4-sec-butylphenyl)-2-(6-fluoropyridin-3-yl)quinazolin-4(3H)-one

HRID 1846344ノート

反応式

HRID 1846344 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:29]=[CH:28][CH:27]=[CH:26][C:12]=1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH2:24][CH3:25])[CH3:23])=[CH:18][CH:17]=1)=[O:14]>CCO>[CH:22]([C:19]1[CH:20]=[CH:21][C:16]([N:15]2[C:13](=[O:14])[C:12]3[C:11](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:10]=[C:8]2[C:5]2[CH:4]=[N:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:17][CH:18]=1)([CH2:24][CH3:25])[CH3:23]

参加物

4

反応物 2

HCID 164142462-Fluoro-5-formylpyridineHCID 167700372-Amino-N-(4-sec-butylphenyl)benzamide

生成物 1

HCID 468417113-(4-sec-butylphenyl)-2-(6-fluoropyridin-3-yl)quinazolin-4(3H)-one収率 15%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-fluoro-5-formylpyridine (0.55 mmol) and anyhydrous CuCl2 (0.150 g, 1.10 mmol) were added to a solution of 2-amino-N-(4-sec-butylphenyl)benzamide (0.205 g, 0.55 mmol) in anyhydrous EtOH (10 mL). After heating at reflux temperature for 2.5 hours, the mixture was 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 2% to 50% EtOAc in heptane, afforded the title compound as a white solid (15%). 1H-NMR (300 MHz, DMSO-d6): δ 8.17-8.33 (m, 2H), 7.87-8.02 (m, 2H), 7.80 (d, J=8.1 Hz, 1H), 7.62-7.66 (m, 1H), 7.23-7.33 (m, 2H), 7.12-7.22 (m, 2H), 6.98-7.11 (m, 1H), 2.54-2.65 (m, 1H), 1.32-1.66 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.60 (t, J=7.4 Hz, 3H). MS (APCI) m/z: 374 (M+H)+.

後処理

  1. temperatureAfter heating
  2. temperatureat reflux temperature for 2.5 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel
  10. washeluting with 2% to 50% EtOAc in heptane

出典と根拠

ORDレコード
ord-d00705f8a2b84700a781fac98d811786
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…