Phenylmethyl N-4-piperidinylcarbamate

A mixture of tert-butyl 4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in (13.1 g, 39.2 mmol), a 5 N aqueous hydrochloric acid solution (40 ml, 200 mmol) and methanol (40 ml) was stirred at mom temperature for 23 hours. (Example 1b) Benzyl N-(piperidin-4-yl)carbamate Piperidin-4-yl-carbamic acid benzyl ester[00457] HCl (10ml, 4M solution in dioxane) was added in one portstirred solution of 4-benzyloxycarbonylamino-piperidine-1 -carboxylic acid te/f-butyl ester (1 .2g, 3.6mmol) in dioxane (5ml) and the suspension was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the reaction was concentrated under vacuum and the resulting solid was collected by filtration, washed with TBME (3 x 100ml) and dried under vacuum to give the title compound (0.74g, 88percent yield) as a white solid.To a solution of compound C13 (6.62 g, 25.83 mmol) in NMP (100 mL) was added compound C14 (18.15 g, 77.5 mmol). The reaction mixture was stirred at 140 C for 16 hours. TLC showed the reaction was complete. The reaction mixture was partitioned between brine (500 mL) and EtOAc (400 mL). The organic layer was washed with water (100 mL x 2), brine (100 mL), dried over anhydrous Na2S04, and concentrated under reduced pressure to give a residue. The residue was purified by Combi Flash to give a brown gum, which was triturated with CH3CN (50 mL) to give compound C15 (2.06 g) as an off-white powder.To a solution of compound G7 (6.62 g, 25.83 mmol) in NMP (100 mL) was added compound G8 (18.15 g, 77.5 mmol). The reaction mixture was stirred at 140 C for 16 hours. TLC showed the reaction was complete. The reaction mixture was partitioned between brine (500 mL) and EtOAc (400 mL). The organic layer was washed with water (100 mL x 2), brine (100 mL), dried over anhydrous Na2S04, and concentrated under reduced pressure to give a residue. The residue was purified by Combi Flash to give a brown gum, which was triturated with CH3CN (50 mL) to give compound G9 (2.06 g) as an off-white powder.into a 250-mL round-bottom flask, was placed tert-butyl N-(4-chloro-3- formylpyridin-2-yl)carbamate (8.1 g, 31.56 mmol, 1.00 equiv), benzyl N-(piperidin-4- yl)carbamate (8.1 g, 34.57 mmol, 1.10 equiv), DIEA (12.2 g, 94.40 mmol, 3.00 equiv), ACN (100 mL). The resulting solution was stirred for 16 h at 85 C and then concentrated under vacuum. The residue was purified by a silica gel column chromatagraph elted with ethyl acetate/petroleum ether (1 :3) to afford 4.6 g (41%) of the title compound as a yellow solid. MS (M+H)+= 355.2.A 5 mL jiW tube equipped with a stir bar was charged with 350 mg of tert-butyl (R)-5-bromo-3-((methyl((5)-5 , 6, 7, 8-tetrahydroquinolin-8-yl)amino)methyl)-3 , 4-dihydroisoquinoline-2( 1H)-carboxylate(0.720 mmol, 1 equiv), 219 mg of

Molecular Weight:234.29
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:234.136827821
Monoisotopic Mass:234.136827821
Topological Polar Surface Area:50.4
Heavy Atom Count:17
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes