1-Boc-2-Methylpiperazine

(RS) tert-butyl 2-methylpiperazine-l-carboxylateA mixture of (RS) tert-butyl 4-benzyl-2-methyl-piperazine-l-carboxylate (3.41 g, 11.7 mmol), ethanol (125 ml) and Pearlman's catalyst (0.854 g, 6.08 mmol) was hydrogenated at 36 psi at ambient temperature overnight. The mixture was filtered and the solids were washed successively with ethanol, DCM and MeOH. The combined filtrate and washings were concentrated in vacuo, redissolved in DCM, then filtered and concentrated in vacuo to give the title compound as a beige oil wt. 2.0 g, 86percent; the NMR spectrum was consistent with that quoted in J. Org. Chem βO 4183 (1995).A solution of 4-benzyl 1-tert-butyl 2-methylpiperazine-1, 4-dicarboxylate (4.8 g, 14.4 mmol) in methanol (25 mL) was added 480 mg of 10percent Pd/C and stirred at room temperature under hydrogen overnight. Filtered and concentrated to give the title product (2.8 g, yield 97percent) as colorless oil. 15Btert-Butyl 2-methylpiperazine- 1 -carboxylate[00728] A solution of 4-benzyl 1-tert-butyl 2-methylpiperazine- 1, 4-dicarboxylate (4.8 g, 14.4 mmol) in methanol (25 mL) was added 480 mg of 10percent Pd/C and stirred at room temperature under hydrogen overnight. Filtered and concentrated to give the title product (2.8 g, yield 97percent) as colorless oil. ^-NMR (400 MHz, CDC110percent palladium carbon (223 mg) was dissolved in ethanol (5 mL) in a solution of 4-benzyl 1-tert-butyl 2-methylpiperazine-1, 4-dicarboxylate (2.23 g, 6.68 mmol) in ethanol (10 mL) . The inside of the reaction vessel was replaced with hydrogen and stirred at room temperature for 3 hours. The reaction solution was filtered through celite and concentrated to give the title compound (1.28 g, 96percent). Transparent oilA solution of tert-butyl piperazine-1-carboxylate (1 g, 5.37 mmol, 1.00 equiv), 6-chloropyridine-3-carbonitrile (690 mg, 4.98 mmol, 1.00 equiv), potassium carbonate (1.4 g, 10.13 mmol, 2.00 equiv), NMP (20 mL) was stirred for 1 h at 80 C. The resulting solution was quenched by 100 ml of water and extracted with 2×100 mL of EtOAc and the organic layers combined and concentrated under vacuum to afforded 1.2 g (78%) of the title compound as yellow oil. LCMS (ESI, m/z): 303.15 [M+H]+A solution of General procedure: A mixture of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (Q1a) (500 mg, 1.8 mmol, 1 eq), the corresponding cyclic amine (8.9 mmol, 5 eq) and DMSO (3.6 mL) was heated by microwave irradiation at 115 C for 3 h. The resultant mixture was concentrated by freeze drying, and to the residue was added EtOAc (30 mL). The precipitate was isolated by vacuum filtration and washed with EtOAc, water and Et2O to afford the Boc-protected aminated quinolone.

Molecular Weight:200.28
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:200.152477885
Monoisotopic Mass:200.152477885
Topological Polar Surface Area:41.6
Heavy Atom Count:14
Complexity:211
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes