Potassium Carbonate → HCID 71678213, compound

HRID 1469750Notes

Reaction equation

HRID 1469750 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]([C:15]([F:18])([F:17])[F:16])[N:3]=1.[CH3:19][C:20]1([CH3:27])[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:19][C:20]1([CH3:27])[CH2:25][CH2:24][CH:23]([NH:26][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]=[C:4]([C:15]([F:18])([F:17])[F:16])[N:3]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4210544,4-Dimethylcyclohexan-1-amineHCID 86692242HCID 86692242, compound

Product 1

HCID 71678213HCID 71678213, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-chloro-8-nitro-2-(trifluoromethyl)quinazoline (200 mg, 0.72 mmol), 4,4-dimethylcyclohexanamine (109 mg, 0.86 mmol), K2CO3 (398 mg, 2.89 mmol) in CH3CN (2 mL) was heated at reflux for 8 h. Then the reaction mixture was quenched with water and 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 120 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.91-8.89 (d, J=7.2 Hz, 1H), 8.69-8.66 (d, J=7.8 Hz, 1H), 8.39-8.37 (d, J=7.8 Hz, 1H), 7.84-7.79 (t, J=8.1 Hz, 1H), 4.12 (m, 1H), 1.76-1.64 (m, 4H), 1.46-1.28 (m, 4H), 0.98 (s, 3H), 0.95 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-b260b3c2c332405a8cad9d4b7b0a0314
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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