Water → HCID 71678046, compound

HRID 1469743

Reaction equation

HRID 1469743 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.[F:15][C:16]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:17]=1[NH2:18].O>C1COCC1>[F:15][C:16]1[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][C:17]=1[NH:18][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

Participants

5

Reactant 3

HCID 962WaterHCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 114584714-Chloro-8-nitroquinazoline

Product 1

HCID 71678046HCID 71678046, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step-2, 150 mg, 0.72 mmol) and 2-fluoro-5-(trifluoromethyl)aniline (387 mg, 2.16 mmol) in THF (4 mL) was heated at 50° C. for 2 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 250 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 10.46 (s, 1H), 8.74-8.71 (d, J=8.7 Hz, 1H), 8.63 (s, 1H), 8.43-8.40 (d, J=7.2 Hz, 1H), 8.01 (d, 1H), 7.86-7.81 (m, 2H), 7.66-7.63 (t, J=9.3 Hz, 1H); MS [M+H]+: 353.14.

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. customseparated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9052b9a546cd4f4abe4e8d8b7c931ab9
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Linked notes

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