2-Chloromethyl-8-methyl-imidazo[1,2-a]pyridine

2-[[4-(2, 4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1, 2-a]pyridine monomaleic acid salt. Refer to Chart E A mixture of 67(D) 8-Methyi-2-(4-(trimethyisiiyi)but-3-ynyl)-imidazo[1, 2-a]pvridine ;To a solution of trimethyl(prop-1-ynyl)silane (259 mg, 2.31 mmol) in THF (7.5 mL) at -78C was added n-BuLi 2.5M in hexane (1.1 mL, 2.8 mmol). After 90min at -78C Step 1. 2-(Chloromethyl)-8-methylimidazo[1, 2-a]pyridine A mixture of 2-amino-3-picoline (Aldrich; 13.23 g), 1, 3-dichloroacetone (Aldrich; 18.92 g), and dimethoxyethane (131 mL) is stirred at room temperature for 2 days. The mixture is then concentrated under reduced pressure and ethanol (100 mL) is added. The mixture is heated at 80 C. for 2.3 h. After cooling, the mixture is concentrated under reduced pressure and the residue is partitioned between saturated aq. sodium bicarbonate and dichloromethane. The combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel first using methanol/dichloromethane (4/96) and a second time using methanol/dichloromethane (2/98). The appropriate fractions are combined and concentrated, and the residue is crystallized from ethyl acetate/dichloromethane/ether to give a first crop of 5.854 g and a second crop of 1.079 g of Reference Production Example 23; 2-(Chlromethyl)-8-methylimidazo [1, 2-a] pyridine; 3. 81 g of 1, 3-dichloroacetone and 3.24 g of 2-amino-3- methylpyridine were dissolved in 30 ml of ethanol, and the solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. To the residue, 50 ml of aqueous saturated sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized from hexane-methyl-t-butyl ether to obtain 1.52 g of 2-(chloromethyl)-8-methylimidazo [1, 2-a] pyridine. H-NMR (CDCl3, TMS, 8 (ppm) ): 2.60 (3H, s), 4.80 (2H, s), 6.68 (1H, t), 6.96 (1H, dd), 7.61 (1H, s), 7.93 (1H, d)Production Example 28; 1.52 g of 2- (chloromethyl)-8-methylimidazo [1, 2- pyridine and 1.36 g of (3, 3, 3- trifluoropropyl) malononitrile were dissolved in 20 ml of N, N-dimethylformamide, and 1.16 g of potassium carbonate was then added under ice-cooling. The mixture was stirred at room temperature for 7 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized form hexane-ethyl acetate to obtain 1.50 g of a compound represented by the following formula: (hereinafter, referred to as the present compound (28)). 1H-NMR (CDCl3, TMS, 8 (ppm) ): 2. 38-2. 42 (2H, m), 2.54-2. 66 (2H, m), 2.57 (3H, s), 3.53 (2H, s), 6.73 (1H, t), 7.00 (1H, dd), 7.66 (1H, s), 7.97 (1H, d)

Molecular Weight:180.63
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:180.0454260
Monoisotopic Mass:180.0454260
Topological Polar Surface Area:17.3
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes