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

HRID 1846344Notes

Reaction equation

HRID 1846344 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-d00705f8a2b84700a781fac98d811786
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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