Water → HCID 71678052, compound

HRID 1469744Notes

Reaction equation

HRID 1469744 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]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.[CH3:22][C:23]1([CH3:30])[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1.O>CC#N>[CH3:22][C:23]1([CH3:30])[CH2:28][CH2:27][CH:26]([NH:29][C:2]2[C:11]3[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 114584714-Chloro-8-nitroquinazolineHCID 241919284,4-Dimethylcyclohexanamine hydrochloride

Product 1

HCID 71678052HCID 71678052, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step-2, 150 mg, 0.72 mmol) in CH3CN (3 mL) were added K2CO3 (300 mg, 2.15 mmol) and 4,4-dimethylcyclohexanamine hydrochloride (352 mg, 2.15 mmol) and the reaction mixture was heated at reflux for 3 h. Then water was added to the reaction mixture and it was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.58-8.55 (d, J=8.4 Hz, 1H), 8.50 (s, 1H), 8.38-8.35 (d, J=7.2 Hz, 1H), 8.25-8.22 (d, J=7.8 Hz, 1H), 7.67-7.61 (t, J=7.8 Hz, 1H), 4.17 (m, 1H), 1.75-1.56 (m, 4H), 1.46-1.18 (m, 4H), 0.98 (s, 3H), 0.95 (s, 3H); MS [M+H]+: 301.20.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. extractionwas extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. customseparated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-31e77130be5f43d6a0b4b67c95c04210
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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