7 (CH, Ar), 126.7 (CH, Ar), 127.4 (CH, Ar), 134.9 (CH, Ar), 149.3 (Cq, Ar), 157.0 (C N), 162.4 (C O), 174.2 (C O); m/z (rel. %): 218 (M+, 25), 200 (46), 173 (100). N-Acetylisatin (1.39 g, 7.4 mmol) was dissolved in about 70 mL of ethanol and 2-aminobenzamide (1.00 g, 7.4 mmol) was added to the solution, covered with a watch glass and then irradiated in a microwave oven at 400 W for a total PD173074 research buy of 10 min. The crude

product was purified using flash chromatography [on silica gel; elution with chloroform–ethyl acetate (1:1)] to afford N-(2-(Z)-4,5-dihydro-3,5-dioxo-3H-benzo[e][1,4]diazepin-2-ylphenyl) acetamide as brown solid (1.18 g, 52%), m.p. 188–191 °C; δH (200 MHz, DMSO-d6) 2.0 (3H, Cilengitide concentration s), 7.20–8.20 (8H, m, ArH), 11.20 (1H, s, NH), 12.50 (1H, s, NH); δC (50 MHz, DMSO-d6) 25.1 (CH3), 121.7 (Cq, Ar), 122.4 (CH, Ar), 123.8 (CH, Ar), 126.5 (CH, Ar), 127.5 (CH, Ar), 127.6 (CH, Ar), 130.3 (CH, Ar), 132.0 (CH, Ar), 135.3 (CH, Ar), 138.4 (Cq, Ar), 148.5 (C N), 153.7 (C O), 162.9 (C O), 168.9 (C O). Oxalic acid dihydrate (0.93 g, 7.4 mmol) was dissolved in 30 mL of ethanol and 2-aminobenzamide (1.00 g, 7.4 mmol)

was added to the resulting solution, stirred to dissolution, covered with a watch glass and then irradiated in a microwave oven at 400 W for a total of 10 min to give a solution, which upon cooling and recrystallization afforded 3,4-dihydro-4-oxoquinazoline-2-carboxylic acid as a white solid (2.04 g, 89%), m.p. 196–198 °C; δH (200 MHz, DMSO-d6) 6.50–8.40 (8H, m, ArH), 8.60 (2H,s, NH), 12.90 (1H, s, OH); δC (50 MHz, DMSO-d6) 115.1 (CH, Ar), 117.1 (CH, Ar), 120.6 (CH, Ar), 121.2 (Cq, Ar), 124.4 (CH,

Ar), 129.4 (CH, Ar), 132.6 (CH, Ar), 133.1 (CH, Ar), 138.8 (Cq, Ar), 150.8 (Cq, Ar), 156.6 (Cq, Ar), 161.7 (C N), 162.2 (C O), 170.9 (C O), 172.0 (C O). 2-Aminobenzamide (1.0 g, 7.4 mmol) was dissolved in 15 ml of acetic acid in a round-bottomed flask. 0.7 mL of bromine was added to the flask and the mixture refluxed for 30 min. On cooling, 40 mL of water was added to the mixture in the flask and refluxed for another 30 min. The product was then filtered hot and finally recrystallized from ethanol to furnish 2-amino-3,5-dibromo-benzamide and as a white solid (1.78 g, 82%), m.p. 210–212 °C; υmax/cm−1 (KBr) 3370, 3184 (NH), 1637 (C O of amide), 1607 (C C); δH (200 MHz, CDCl3) 6.80 (2H, s, NH, D2O exchangeable), 7.50 (1H, s, NH, D2O exchangeable), 7.70 (1H, s, ArH), 7.80 (1H, s, ArH), 8.10 (1H, s, NH, D2O exchangeable); δC (50 MHz, CDCl3) 105.7 (Cq, Ar), 111.1 (Cq, Ar), 117.5 (Cq, Ar), 131.4 (CH, Ar), 137.3 (CH, Ar), 146.6 (Cq, Ar), 170.0 (C O); m/z (rel.