5,7-dichloroiMidazo[1,2-c]pyriMidine

5, 7-Dichloroimidazo[1, 2-c]pyrimidine 38.3 g (225.86 mmol) of 7-chloroimidazo[1, 2-c]pyrimidin-5-ol are suspended in 450.2 g (2936 mmol) of phosphoryl chloride under argon and heated at 120° C. for 4 h. After this time, the excess phosphoryl chloride is removed in vacuo, and the residue is distilled together with toluene. The residue is suspended in water, the pH is brought to 7 with saturated aqueous sodium bicarbonate solution, and the precipitated solid is filtered off with suction. The latter is washed with water and dried over phosphorus pentoxide for 18 h. 33.5 g (67percent of theory) of the product are obtained as a solid.LCMS (method 6): RGeneral procedure: To a solution of Example 4A (60 mg, 0.21 mmol) in N, N-dimethylformamide (1 mL) was added N, N-diisopropylethylamine (0.18 mL, 1.05 mmol) and 2-bromo-5-methyl-1, 3, 4- oxadiazole (37.8 mg, 0.22 mmol). The reaction mixture was stirred for 72 hours at 80 C. The mixture was then purified with preparative HPLC [Waters XBridge C185 mum OBD column, 30 × 100 mm, flow rate 40 mL/minute, 5-100% gradient of acetonitrile in buffer (0.1 % trifluoroacetic acid)] to give the title compound (36 mg, 0.098 mmol, 47% yield). The reaction and purification conditions described in Example 294 substituting 5, 7- dichloroimidazo[1, 2-c]pyrimidine for 2-bromo-5-methyl-1, 3, 4-oxadiazole gave the title compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.41 (s, 1H), 8.82 (s, 1H), 8.11 (d, J = 2.0 Hz, 1H), 7.83 (d, J = 2.0 Hz, 1H), 7.47 (t, J = 8.9 Hz, 1H), 7.17 (s, 1H), 7.06 (dd, J = 11.4, 2.9 Hz, 1H), 6.84 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.49 (s, 2H), 2.44 (s, 6H); 19F NMR (376 MHz, DMSO-d6) delta ppm -74.32, -114.09; MS (ESI+) m/z 436 (M+H)+.Example 17A; N6-{2-[7-Chloroimidazo[1, 2-c]pyrimidin-5-yl)amino]ethyl}-3-nitropyridine-2, 6-diamine 800 mg (4.13 mmol) of Example 16A; 6-({2-[(7-Chloroimidazo[1, 2-c]pyrimidin-5-yl)amino]ethyl}amino)nicotinonitrile 707 mg (3.20 mmol) of

Molecular Weight:188.01
XLogP3:3
Hydrogen Bond Acceptor Count:2
Exact Mass:186.9704025
Monoisotopic Mass:186.9704025
Topological Polar Surface Area:30.2
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes