Method for producing 1,2-dihydropyridine-2-one compound
The present inventions provide a method for commercially producing a 1,2 -dihydropyridine-2-one compound represented by the following formula (III-a) wherein the ring A represents an optionally substituted 2-pyridyl group, the ring B represents an optionally substituted phenyl group, and the ring C represents an optionally substituted phenyl group. Further, the invention provides crystals of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2 -dihydropyridin-2-one and production processes therefore.
1. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 10.3° in a powder X-ray diffraction.
2. The crystal according to claim 1 further having a diffraction peak at a diffraction angle (2θ±0.2°) of 19.1° in a powder X-ray diffraction.
3. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having peaks at chemical shifts of around 149.0 ppm and around 125.6 ppm in a 13 C Solid State Nuclear Magnetic Resonance spectrum.
4. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 16.7° in a powder X-ray diffraction.
5. The crystal according to claim 4 further having diffraction peaks at diffraction angles (2θ±0.2°) of 12.9° and 24.9° in a powder X-ray diffraction.
6. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having an absorption peak at a wavenumber of 1658±1 cm −1 in an infrared absorption spectrum (KBr method).
7. The crystal according to claim 6 further having an absorption peak at a wavenumber of 501±1 cm −1 in an infrared absorption spectrum (KBr method).
8. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having peaks at chemical shifts of around 145.9 ppm and around 137.7 ppm in a 13 C Solid State Nuclear Magnetic Resonance spectrum.
9. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having diffraction peaks at diffraction angles (2θ±0.2°) of 23.7° and 25.0° in a powder X-ray diffraction.
10. The crystal according to claim 6 further having diffraction peaks at diffraction angles (2θ±0.2°) of 5.7° and 9.5° in a powder X-ray diffraction.
11. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 10.3°, 14.2° and 19.1° in a powder X-ray diffraction.
12. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 7.8°, 9.5°, 10.3°, 14.2°, 15.1°, 16.1°, 19.1° and 20.5° in a powder X-ray diffraction.
13. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having peaks at chemical shifts of around 160.0 ppm, 152.8 ppm, 152.0 ppm, 149.0 ppm, 140.5 ppm, 137.0 ppm, 134.7 ppm, 133.4 ppm, 131.0 ppm, 129.5 ppm, 128.2 ppm, 127.0 ppm, 125.6 ppm, 120.3 ppm, 118.2 ppm, 114.6 ppm and 108.2 ppm in a 13 C Solid State Nuclear Magnetic Resonance spectrum.
14. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 12.9°, 16.7° and 24.9° in a powder X-ray diffraction.
15. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 8.0°, 9.2°, 10.0°, 12.9°, 16.7°, 18.4°, 18.8°, 20.7° and 24.9° in a powder X-ray diffraction.
16. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having peaks at chemical shifts of around 159.7 ppm, 151.2 ppm, 145.9 ppm, 139.9 ppm, 137.7 ppm, 134.9 ppm, 132.8 ppm, 131.7 ppm, 130.1 ppm, 129.0 ppm, 128.2 ppm, 127.3 ppm, 126.8 ppm, 125.8 ppm, 121.1 ppm, 120.6 ppm, 119.1 ppm, 114.2 ppm and 109.4 ppm in a 13 C Solid State Nuclear Magnetic Resonance spectrum.
17. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having an absorption peak at a wavenumber of 3447.1±0.1 cm −1 , 3066.3±0.1 cm −1 , 2221.6±0.1 cm −1 , 1657.5±0.1 cm −1 , 1585.2±0.1 cm −1 , 1476.2±0.1 cm −1 and 785.9±0.1 cm −1 in an infrared absorption spectrum (KBr method).
18. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having an absorption peak at a wavenumber of 3447.1±0.1 cm −1 , 3066.3±0.1 cm −1 , 2221.6±0.1 cm −1 , 1657.5±0.1 cm −1 , 1619.0±0.1 cm −1 , 1585.2±0.1 cm −1 , 1565.9±0.1 cm −1 , 1549.5±0.1 cm −1 , 1476.2±0.1 cm −1 , 1434.8±0.1 cm −1 , 1368.3±0.1 cm −1 , 1318.1±0.1 cm −1 , 1266.0±0.1 cm −1 , 1247.7±0.1 cm −1 , 1157.1±0.1 cm −1 , 1135.9±0.1 cm −1 , 1097.3±0.1 cm −1 , 933.4±0.1 cm −1 , 896.7±0.1 cm −1 , 879.4±0.1 cm −1 , 785.9±0.1 cm −1 , 753.1±0.1 cm −1 , 729.9±0.1 cm −1 , 694.3±0.1 cm −1 630.6±0.1 cm −1 , 603.6±0.1 cm −1 , 556.4±0.1 cm −1 , 501.4±0.1 cm −1 and 443.6±0.1 cm −1 in an infrared absorption spectrum (KBr method).
19. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 5.7°, 9.5°, 23.7° and 25.0° in a powder X-ray diffraction.
20. An anhydrous crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one having a diffraction peak at a diffraction angle (2θ±0.2°) of 5.7°, 7.7°, 8.7°, 9.5°, 11.6°, 12.4°, 17.6°, 23.7° and 25.0° in a powder X-ray diffraction.