Water → HCID 86692240, compound

HRID 1469746Notes

Reaction equation

HRID 1469746 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:19]([NH2:20])=[CH:18][C:17]=1[C:23]([F:26])([F:25])[F:24].O>C1COCC1>[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][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)=[CH:18][C:17]=1[C:23]([F:24])([F:25])[F:26]

Participants

5

Reactant 3

HCID 962WaterHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 114584714-Chloro-8-nitroquinazoline

Product 1

HCID 86692240HCID 86692240, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-8-nitroquinazoline (Intermediate-7, step-2, 200 mg, 0.95 mmol) and 4-fluoro-3-(trifluoromethyl)aniline (510 mg, 2.85 mmol) in THF (4 mL) was stirred at rt 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 10.47 (s, 1H), 8.83-8.80 (d, J=8.4 Hz, 1H), 8.72 (s, 1H), 8.42-8.39 (d, J=7.8 Hz, 1H), 8.31-8.25 (m, 2H), 7.86-7.81 (t, J=7.8 Hz, 1H), 7.64-7.58 (t, J=9.6 Hz, 1H).

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-9e8f1e7de0ad4ac5b2350a86160d925d
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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