Hydrochloric Acid → 1-Cyclopropylmethyl-4-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-a]quinazolin-5-yl]piperazin-2-one

A solution of 3-(2-fluorophenyl)-5-(4-methylbenzenesulfonyloxy)-[1,2,3]triazolo[1,5-α]quinazoline (0.10 g, 0.23 mmol), triethylamine (1 ml, 7.2 mmol) and 1-cyclopropylmethylpiperazin-2-one.HCl (0.22 g, 1.15 mmol) in dry N,N-dimethylformamide (2 ml) was stirred at 50° C. under nitrogen for 18 h. The mixture was cooled, then diluted with water (15 ml) and extracted with EtOAc (2×75 ml). The combined organic extracts were washed with brine, dried over MgSO4 and evaporated to give a brown oil. Purification by preparative thin layer chromatography eluting with CH2Cl2:MeOH (93:7) gave 1-cyclopropylmethyl-4-[3-(2-fluorophenyl)-[1,2,3]triazolo[1,5-α]quinazolin-5-yl]piperazin-2-one (0.020 g, 21%) as a white solid. δH (400 MHz; CDCl3) 0.26-0.31 (2H, m), 0.52-0.58 (2H, m), 0.99-1.05 (1H, m), 3.37 (2H, d, J=7), 3.77 (2H, dd, J=5 and 5), 3.97 (2H, dd, J=5 and 5), 4.39 (2H, s), 7.20-7.31 (2H, m), 7.35-7.41 (1H, m), 7.66 (1H, dd, J=7 and 7), 7.94 (1H, dd, J=8 and 8), 8.02-8.11 (2H, m), 8.72 (1H, d, J=8); m/z (ES+) 417 (M+H+).

1. temperatureThe mixture was cooled
2. extractionextracted with EtOAc (2×75 ml)
3. washThe combined organic extracts were washed with brine
4. dry with materialdried over MgSO4
5. customevaporated
6. customto give a brown oil
7. customPurification by preparative thin layer chromatography
8. washeluting with CH2Cl2:MeOH (93:7)

ORDレコード

ord-ebba54701d5d49d7a394d9df2e5a8325

出典データセット

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06730681B2