Ethanamine, N-methyl-, hydrochloride (1:1)

yellow adhering crystalline powder

General procedure: Boc-Val-OH 19 (1.5 equiv) was dissolved in 3 mL DMF. To this was added HATU (2 equiv) and DIEA (5 equiv) to generate the activated ester prior to the addition of the appropriate N-alkyl methylamine hydrochloride 21a-d (1 equiv). The reaction mixture was stirred at 50 under nitrogen overnight. The reaction was diluted with water and extracted with EtOAc (5 × 50 mL). The combined organic extract was dried over anhydrous Na2SO4, filtered through a bed of celite and concentrated in vacuo. The crude product was purified using flash silica gel column chromatography (50% EtOAc: 50% pet. ether), and the target compound obtained on vacuum concentration.The title compound (188):In accordance with the method described in Example 106, using Intermediate 252 (134.0mg, 0.2mmol) and N- methylethylamine hydrochloride (35.5mg, 0.6mmol) was prepared. Intermediate 246 (131mg, 0.2mmol) and lithium hydroxide (14.4mg, 0.6mmol) were mixed and 2 ml THF was added 2mL of water, at room temperature the reaction 30min. Evaporated under reduced pressure THF, 1M hydrochloric acid to pH, precipitated, filtered and dried. The resulting white solid with DIC (63muL, 0.4mmol), HOSu (46mg, 0.4mmol) were mixed in 2mLTHF reaction at room temperature 12h. Was added dimethylamine (422muL, 2MinTHF, 0.6mmol), the reaction was continued 1h. Column chromatography on silica gel, DCM / MeOH as eluent to give 81mg as a pale yellow solid, yield 60.6percent.To a solution of Preparation AI (0.7 g, 1.67 mmol) in methanol was added diisopropylethylamine (0.43 g, 3.3 mmol) followed by ethylmethylamine.HCl (0.19 g, 3.35 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh) using 20percent ethyl acetate in pet-ether as mobile phase to give 2-chloro-N-ethyl-8-(4-fluorophenyl)-7-(4-methoxybenzyl)-N-methyl- 5, 6, 7, 8-tetrahydropyrido[3, 4-d]pyrimidin-4-amine (0.40 g, 54percent) as off-white solid. LC- MS (M+H)+ = 441.2. 1H NMR: (400 MHz, DMSO-d6) delta ppm 7.49 (2H, m), 7.19-7.14 (4H, m), 6.87 (2H, m), 4.42 (IH, s), 3.73 (3H, s), 3.55 (2H, m), 3.42 (IH, m), 3.21 (IH, m), 3.04 (3H, s), 2.95 (2H, m), 2.56 (IH, m), 2.25 (IH, m), 1.16 (3H, t , J= 7.2 Hz).Preparation Alb2-chloro-N-ethyl-8-(4-fluorophenyl)-7-(4-methoxybenzyl)-N-methyl-5, 6, 7, 8- tetrahydropyrido[3, 4-d]pyrimidin-4-amineTo a solution of Preparation AI (0.7 g, 1.67 mmol) in methanol was added diisopropylethylamine (0.43 g, 3.3 mmol) followed by ethylmethylamine.HCl (0.19 g, 3.35 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh) using 20percent ethyl acetate in pet-ether as mobile phase to give 2-chloro-N-ethyl-8-(4-fluorophenyl)-7-(4-methoxybenzyl)-N-methyl- 5, 6, 7, 8-tetrahydropyrido[3, 4-d]pyrimidin-4-amine (0.40 g, 54percent) as off-white solid. LC- MS (M+H)+ = 441.2. 3/4 NMR: (400 MHz, DMSO-d6) delta ppm 7.49 (2H, m), 7.19-7.14 (4H, m), 6.87 (2H, m), 4.42 (1H, s), 3.73 (3H, s), 3.55 (2H, m), 3.42 (1H, m), 3.21 (1H, m), 3.04 (3H, s), 2.95 (2H, m), 2.56 (1H, m), 2.25 (1H, m), 1.16 (3H, t , J= 7.2 Hz).To a solution of Preparation O (0.20 g, 0.61 mmol) in methanol was added diisopropylethylamine (0.172 g, 1.3 mmol) followed by addition of Preparation Ob2-chloro-N-ethyl-8-(4-fluorophenyl)-N-methyl-6, 8-dihydro-5H-pyrano[3, 4-d]pyrimidin- -amineTo a solution of Preparation O (0.20 g, 0.61 mmol) in methanol was added diisopropylethylamine (0.172 g, 1.3 mmol) followed by addition of

Molecular Weight:95.57
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:95.0501770
Monoisotopic Mass:95.0501770
Topological Polar Surface Area:12
Heavy Atom Count:5
Complexity:7.2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes