7-BROMO-1H-QUINAZOLIN-4-ONE

0.0 g (1.56 mol) of 2-amino-4-bromobenzoic acid were suspended in 970 ml of formamide and subsequently stirred at 170° C. for 12 h. Conventional work-up gave 326.0 g of 7-bromo-3H-quinazolin-4-one; HPLC/MS (M+H)7-bromoquinazolin-4(3H)-oneA mixture of 2-amino-4-bromobenzoic acid (2.0 g) and formamide (1.5 ml) was stirred while heating at 140-145 C. After 4 hours, the reaction mixture was cooled, and 30 ml of water was added causing a solid to precipitate. After collection by filtration, the crude product was pure enough to be used in the next step without further purification. Yield: 1.47 g (6.53 mmol, 71percent). 1H NMR (250 MHz, DMSO) ' (ppm) 8.14 (d, J= 3.0 Hz, 1 H), 8.05 (d, J= 8.5 Hz, 1 H), 7.90 (d, J= 1.9 Hz, 1 H), 7.70 (dd, J= 1.9 Hz, J= 8.5 Hz, 1 H).2-amino-4-bromobenzoic acid (Compound 4) was reacted with formamide to give 7-bromoquinazolin-4 (3H) -one (Compound 5)5.0 g (23.14 mmol) of 2-amino-4-bromobenzoic acid (Compound 4) was dissolved in 80 ml (2. Olmmol) formamide, Under the protection of nitrogen at 150 ° C, power 300W microwave conditions, reaction 1.45h, after the end of the reaction, the reaction solution by adding ice water, And the mixture was extracted three to four times with ethyl acetate. The extracted organic phase was washed successively with a saturated sodium hydrogencarbonate solution and saturated brine, Dried over sodium sulphate and dried to give a reddish-brown residue, which was chromatographed to give a red brown solid, 7-bromoquinazolin-4 (3H) -one (compound 5), 1.898 in 36.3percent yield;7-Bromoquinazolin-4(3H)-one (compound A.1) To a solution of 2-amino-4-bromo-benzamide (1 equiv) in DMA (0.14 M) were added triethyl orthoformate (10 equiv) and trifluoroacetic acid (1 equiv). The reaction vessel was sealed and exposed to microwave radiation (160 2-Amino-4-bromobenzamide (107 mg, 0.5 mmol), [Cp * Ir (2, 2'-bpyO) (H2O)](5.4 mg, 0.005 mmol, 1 molpercent), Cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.) And methanol (0.5 ml) were sequentially added to a dried 5 mL microwave reaction tube.The tube was nitrogen protected and placed in a single mode pressure microwave synthesizer (Discover CEM, USA). After the reaction mixture was reacted at 130 ° C for 2 hours, it was cooled to room temperature. Rotary evaporation to remove the solvent, Pure target compound was then obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 80percent2) 4-Bromoanthranilic amide (40 g, 186 mmol) obtained in 1) was dissolved in ethanol (400 mL). Thereto was added sodium methoxide (54.2 g, 93 mmol) with stirring under ice-cooling and then ethyl formate (60.1 mL, 744 mmol) was added dropwise. The mixture was heated under reflux for 1.5 hrs. The reaction mixture was allowed to cool to room temperature and water (500 mL) was added and then acetic acid (40 mL) was added. The mixture was concentrated under reduced pressure and water (200 mL) was added. The precipitate was collected by filtration and dried to give 7-bromo-3H-quinazolin-4-one (35 g, 156 mmol, 84percent). 7-bromo-3H-quinazolin-4-one [0153] 1H NMR (DMSO-d6) δ ppm: 7.68 (dd, J=1.7, 8.5 Hz, 1H), 7.88 (d, J=1.7 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 8.14 (s, 1H).3) Formamidine acetate (1.96 g, 18.9 mmol) and 2-ethoxyethanol (25 mL) were added to 4-bromoanthranyl acid (1.63 g, 7.55 mmol) and the mixture was heated under reflux for 7 hrs. Formamidine acetate (1.45 g) was added and the mixture was further refluxed for 6 hrs. Dilute aqueous ammonia solution (30 mL) was added, and after stirring for a while, the product was collected by filtration and dried to give the objective 7-bromo-3H-quinazolin-4-one (1.67 g, 98percent). [CHEMMOL-00362] [0144] 1H NMR (DMSO-d6) δ ppm: 7.69 (dd, J=1.9, 8.4 Hz, 1H), 7.89 (d, J=1.9 Hz, 1H), 8.04 (d, J=8.4 Hz, 1H), 8.14 (br s, 1H).(23.14 mmol) of 2-amino-4-bromobenzoic acid was dissolved in 80 ml (2.01 mmol) of formamide and reacted under nitrogen at 150 ° C under a microwave power of 300 W for 1.45 h. After completion of the reaction, The reaction solution was added to ice water and extracted with ethyl acetate for 3-4 times. The extracted organic phase was washed successively with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then spin dried to give a reddish brown residue , And the reddish brown residue was separated on a chromatographic column to give 1.89 g of a reddish brown solid 7-bromoquinazolin-4 (3H) -one in 36.3percent yield.Around bottom two flask charged with 2-amino-5-bromobenzoicacid 12 (5.00 g, 23.14 mmol) was flushed with nitrogen and suspended in HCONH

Molecular Weight:225.04
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:223.95853
Monoisotopic Mass:223.95853
Topological Polar Surface Area:41.5
Heavy Atom Count:12
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes