Electric Literature of 6000-50-6 ,Some common heterocyclic compound, 6000-50-6, molecular formula is C7H10Cl2N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (CAS-No. 6000-50-6, 214 mg, 1.11 mmol) was added to a suspension of raw 4-nitrophenyl {4-[6-oxo-5-(quinolin-5-yl)-1,4,5,6- tetrahydropyridazin-3-yl]phenyl}carbamate (356 mg, 740 mumol) in dichloromethane (14 mL) and N,N-diisopropylethylamine (640 mul, 3.7 mmol). After stirring at r. t. for 2h the mixture was cooled to -20C and the precipitate was filtered off after standing for 12h and washed with cold dichloromethane. The precipitate was stirred in aqueous sodium hydroxide (20 mL, 1M), filtered, washed with water and dried under reduced pressure to give 175 mg (67% purity, 51% yield) of the title compound containing N-{4-[6-oxo-5-(quinolin-5-yl)-1,6- dihydropyridazin-3-yl] phenyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide as minor impurity. (0693) LC-MS (Method 2): Rt = 0.78 min; MS (ESIpos): m/z = 463 [M+H]+ (0694) 1H-NMR (400MHz, DMSO-d6) delta [ppm]: 3.29 (dd, 1H), 3.42 (dd, 1H), 4.72 (dd, 1H), 4.81 (br d, 4H), 7.43 (d, 1H), 7.52 (d, 1H), 7.56 (dd, 1H), 7.60 – 7.65 (m, 2H), 7.68 – 7.76 (m, 3H), 7.97 (d, 1H), 8.50 (d, 1H), 8.58 – 8.64 (m, 3H), 8.92 (dd, 1H), 11.20 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6000-50-6, its application will become more common.
Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
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