Benzenamine, 4-(1-methylpropyl)- → HCID 58532510, compound

HRID 1846272Notes

Reaction equation

HRID 1846272 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2O[C:10](=[O:18])[C:11]3[CH:17]=[N:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[C:4]([CH3:19])[C:3]=1[O:20][C:21](=[O:23])[CH3:22].[CH:24]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)([CH2:26][CH3:27])[CH3:25]>C(O)(=O)C>[CH:24]([C:28]1[CH:29]=[CH:30][C:31]([N:32]2[C:10](=[O:18])[C:11]3[CH:17]=[N:16][CH:15]=[CH:14][C:12]=3[N:13]=[C:8]2[C:6]2[CH:5]=[C:4]([CH3:19])[C:3]([O:20][C:21](=[O:23])[CH3:22])=[C:2]([CH3:1])[CH:7]=2)=[CH:33][CH:34]=1)([CH2:26][CH3:27])[CH3:25]

Participants

4

Reactant 2

HCID 121771Benzenamine, 4-(1-methylpropyl)-HCID 58532501HCID 58532501, compound

Product 1

HCID 58532510HCID 58532510, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of acetic acid 2,6-dimethyl-4-(4-oxo-4H-pyrido[4,3-d][1,3]oxazin-2-yl)-phenyl ester (1.04 g, 3.35 mmol) in glacial acetic acid (20 mL) was added 4-(sec-butyl)-aniline (B) (0.750 g, 5.02 mmol). The reaction mixture was stirred at 120° C. for 60 hours under nitrogen and cooled to room temperature. Acetic acid was removed under reduced pressure. The residue was diluted with water (100 mL), neutralized to pH 7 with saturated aqueous NaHCO3 solution, and extracted with ethyl acetate (200 mL). The organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. Solvent was evaporated and the crude compound was purified by column chromatography (silica gel 230-400 mesh; 20-30% ethyl acetate in hexanes as eluent) to give acetic acid 4-[3-(4-sec-butyl-phenyl)-4-oxo-3,4-dihydro-pyrido[4,3,d]pyrimidin-2-yl]-2,6-dimethyl-phenyl ester (7) as a white solid. Yield: 0.580 g (39%).

Workup

  1. temperaturecooled to room temperature
  2. customAcetic acid was removed under reduced pressure
  3. additionThe residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (200 mL)
  5. washThe organic phase was washed with water (100 mL)
  6. dry with materialbrine (100 mL), and dried over anhydrous Na2SO4
  7. customSolvent was evaporated
  8. customthe crude compound was purified by column chromatography (silica gel 230-400 mesh; 20-30% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-e198cfebc9af481e95190ee80f0b64b1
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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