Quinazoline compounds
A compound, optionally a technology, applied in the direction of active ingredients of heterocyclic compounds, drug combinations, organic chemistry, etc., can solve the problems of inflammation and inhibition of pro-inflammatory gene expression, etc.
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[0709] The preparation of representative compounds of the invention is illustrated below. Compounds described as homogeneous were determined to have a purity of 90% or greater (excluding enantiomers) by analytical reverse phase chromatography using 254 nM UV detection. Melting points are reported in uncorrected degrees Celsius. Mass spectral data are reported as mass-to-charge ratio m / z; and for high-resolution mass spectral data, calculated and experimentally measured masses [M+H] for neutral formula M + Report. All reactions were stirred and performed under nitrogen atmosphere unless otherwise stated.
example 1
[0711] 4-(3-Methoxyphenyl)-8-(trifluoromethyl)quinazoline
[0712] A stirred mixture of (2-amino-3-(trifluoromethyl)phenyl)(3-methoxyphenyl)methanone (2.95 g, 10.0 mmol), formic acid (5 mL) and formamide (20 mL) Heated at 150 °C for 4 h under a nitrogen atmosphere. After 1 h, the reaction was cooled, poured into ice water (150 mL), and extracted with dichloromethane (2 x 50 mL). The combined extracts were dried (MgSO 4 ) and concentrated in vacuo. Chromatography on silica gel (gradient 15 / 85 to 30 / 70 E / H) afforded the title compound (1.04 g, R in 35 / 65 E / H) as a white solid. f approximately equal to 0.5). MS (ES) m / z 304.6; HRMS: C 16 h 11 f 3 N 2 O+H + The calculated value of is 305.08962; the experimental value (ESI, [M+H] + ) is 305.0896.
example 2
[0714] 3-(8-(trifluoromethyl)quinazolin-4-yl)phenol
[0715] A stirred mixture of 4-(3-methoxyphenyl)-8-(trifluoromethyl)quinazoline (915mg, 3.00mmol) and pyridine hydrochloride (6.5g) was heated at 200-205°C in Heated under nitrogen atmosphere. After 2.5 h, the reaction was poured into water (50 mL), washed with saturated NaHCO 3 The aqueous solution (100 mL) was treated and extracted with dichloromethane (100 mL). The combined extracts were dried (MgSO 4 ) and concentrated in vacuo. Chromatography on silica gel (30 / 70 to 60 / 40E / H gradient) afforded the title compound (810 mg, R in 50 / 50E / H) as a white solid. f approximately equal to 0.3). MS (ES) m / z 290.9.
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