HCID 86692243, compound → HCID 86692259, compound

HRID 1469779Notes

Reaction equation

HRID 1469779 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:15])[N:3]=1>C(N)(C)C.O>[CH:6]([NH:5][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:15])[N:3]=1)([CH3:11])[CH3:7]

Participants

4

Reactant 1

HCID 86692243HCID 86692243, compound

Product 1

HCID 86692259HCID 86692259, compoundYield 108.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6363IsopropylamineSolvent

Procedure

A solution of 4-chloro-2-methyl-8-nitroquinazoline (Intermediate-27, step-2, 100 mg, 0.45 mmol) in isopropylamine (1 mL) was heated at reflux for 30 mins. Then the reaction mixture was diluted with water and was extracted with ethyl acetate. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 60 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.54-8.51 (d, J=8.4 Hz, 1H), 8.23-8.21 (d, J=7.5 Hz, 1H), 8.17-8.14 (d, J=7.8 Hz, 1H), 7.56-7.51 (t, J=7.8 Hz, 1H), 4.58-4.51 (m, 1H), 2.44 (s, 3H), 1.27 (s, 3H), 1.25 (s, 3H).

Workup

  1. temperatureat reflux for 30 mins
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3507b1f51abc4e0586693c0e19455a9b
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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