Ethylamine → 2-(4-Chloro-2-ethylsulfanylphenyl)-4-ethylamino-7-trifluoromethylquinazoline

HRID 1775268Notes

Reaction equation

HRID 1775268 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl[C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][CH:13]=2)[N:8]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[S:26][CH2:27][CH3:28])[N:6]=1>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:7]2[N:6]=[C:5]([NH:3][CH2:1][CH3:2])[C:14]3[C:9](=[CH:10][C:11]([C:15]([F:17])([F:16])[F:18])=[CH:12][CH:13]=3)[N:8]=2)=[C:20]([S:26][CH2:27][CH3:28])[CH:21]=1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 1180355764-Chloro-2-(4-chloro-2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline

Product 1

HCID 1180350832-(4-Chloro-2-ethylsulfanylphenyl)-4-ethylamino-7-trifluoromethylquinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 ml of ethylamine (a 70% aqueous solution) was added to a mixture of 600 mg of 4-chloro-2-(4-chloro-2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline and 10 ml of THF, and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium bicarbonate solution was added to the residue, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure to obtain 606 mg of 2-(4-chloro-2-ethylsulfanylphenyl)-4-ethylamino-7-trifluoro methylquinazoline (Compound of Present Invention 15).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium bicarbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50e37514985f4047b687cf04f82dbdc8
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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