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

HRID 1846344노트

반응식

HRID 1846344 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d00705f8a2b84700a781fac98d811786
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952021B2

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