6-BOC-3,6-DIAZABICYCLO[3.2.0]HEPTANE

3-Benzyl, 6-tert-butyl-3, 6-diazabicyclo[3.2.0]heptane-3, 6-dicarboxylate (2.61 mmol) in a Parr bottle was taken up in MeOH (0.1 M). Pd/C (5percentwt- 61 .1 percent HStep I. 3, 6-Diaza-bicyclo[3.2.0]heptane-6-carboxylic acid tert-butyl ester. 3-Benzyl, 6-tert-butyl-3, 6-diazabicyclo[3.2.0]heptane-3, 6-dicarboxylate (2.61 mmol) in a Parr bottle was taken up in MeOH (0.1 M). Pd/C (5percentwt- 61 .1 percent H2O from Johnson Mathey, 60 mg) was added. The mixture was placed on the Parr shaker and air was removed via vacuum. The system was purged a few time with nitrogen and then allowed to shake at 15 PSI for ~1 .5 hr. TLC showed that all the starting material was consumed. The mixture was filtered through a pad of Celite. The filtrate was concentrated to provide a viscous clear residue, II in 66.1 percent. Material was clean enough to carry forward without purification. MS (ESI) mass calcd. for Ci0Hi8N2O2, 198.26; m/z found, 199.2 [M+H]+. 1H NMR (400 MHz, CDCI3) 4.73 - 4.50 (m, 1 H), 3.98 (t, J = 8.3, 1 H), 3.46 - 3.15 (m, 2H), 3.09 - 2.99 (m, 1 H), 2.93 - 2.82 (m, 1 H), 2.73 - 2.62 (m, 1 H), 2.53 - 2.42 (m, 1 H), 2.31 (s, 1 H), 1 .43 (s, 9H).In a sealed tube, 7-fluoro-2-(2-methyl-[l, 2, 4]triazolo[l, 5-a]pyrimidin-6-yl)-4H-pyrido[l, 2- a]pyrimidin-4-one (Intermediate (VI-1), 25.4 mg, 0.169 mmol, 1 eq.), and tert-butyl 3, 6- diazabicyclo[3.2.0]heptane-6-carboxylate (100 mg, 0.506 mmol, 3 eq.) were stirred in DMSO (2 ml) at 120C for 48 hours. The crude was purifed by preparative HPLC. (0364) The isolated solid was then treated following the General Procedure 1 for Boc deprotection to afford the product 7-(3, 6-diazabicyclo[3.2.0]heptan-3-yl)-2-(2-methyl-[l, 2, 4]triazolo[l, 5- a]pyrimidin-6-yl)-4H-pyrido[l, 2-a]pyrimidin-4-one 2, 2, 2-trifluoroacetate (12.4 mg, 0.025 mmol, 73.9 % yield) as a yellow solid.Step A: Intermediate 2 (0.51 mmol), 2-chloro-quinoxaline (0.51 mmol) and K2CO3 (1 .53 mmol) were taken up in DMF (0.2 M). The mixture heated to 80 C and allowed to heat at 80 C overnight. The mixture was cooled to room temperature, diluted with water, and extracted with diethyl ether (3 X 100 mL). The organics were combined, dried over MgSO4, filtered, and concentrated. The resulting crude product was purified by flash column chromatography (FCC) (50-100% EtOAc/hex) to provide 3-quinoxalin-2-yl-3, 6-diaza- bicyclo[3.2.0]heptane-6-carboxylic acid tert-butyl ester (84%). MS (ESI) mass calcd. for Ci8H22N4O2, 326.39; m/z found, 327.2 [M+H]+. 1 H NMR (400 MHz, CDCIs): 8.48 (s, 1 H), 7.93 - 7.87 (m, 1 H), 7.76 - 7.69 (m, 1 H), 7.62 - 7.55 (m, 1 H), 7.45 - 7.36 (m, 1 H), 4.90 (br s, 1 H), 4.41 (br s, 1 H), 4.27 - 4.09 (m, 2H), 3.68 - 3.61 (m, 1 H), 3.49 - 3.41 (m, 1 H), 3.34 - 3.20 (m, 2H), 1 .45 (br s, 9H).3-Benzyl, 6-tert-butyl-3, 6-diazabicyclo[3.2.0]heptane-3, 6-dicarboxylate (2.61 mmol) in a Parr bottle was taken up in MeOH (0.1 M). Pd/C (5%wt- 61 .1 % H2O from Johnson Mathey, 60 mg) was added. The mixture was placed on the Parr shaker and air was removed via vacuum. The system was purged a few time with nitrogen and then allowed to shake at 15 PSI for ~1 .5 hr. TLC showed that all the starting material was consumed. The mixture was filtered through a pad of Celite. The filtrate was concentrated to provide a viscous clear residue, II in 66.1 %. Material was clean enough to carry forward without purification. MS (ESI) mass calcd. for Ci0Hi8N2O2, 198.26; m/z found, 199.2 [M+H]+. 1H NMR (400 MHz, CDCI3) 4.73 - 4.50 (m, 1 H), 3.98 (t, J = 8.3, 1 H), 3.46 - 3.15 (m, 2H), 3.09 - 2.99 (m, 1 H), 2.93 - 2.82 (m, 1 H), 2.73 - 2.62 (m, 1 H), 2.53 - 2.42 (m, 1 H), 2.31 (s, 1 H), 1 .43 (s, 9H).Step I. 3, 6-Diaza-bicyclo[3.2.0]heptane-6-carboxylic acid tert-butyl ester. 3-Benzyl, 6-tert-butyl-3, 6-diazabicyclo[3.2.0]heptane-3, 6-dicarboxylate (2.61 mmol) in a Parr bottle was taken up in MeOH (0.1 M). Pd/C (5%wt- 61 .1 % H2O from Johnson Mathey, 60 mg) was added. The mixture was placed on the Parr shaker and air was removed via vacuum. The system was purged a few time with nitrogen and then allowed to shake at 15 PSI for ~1 .5 hr. TLC showed that all the starting material was consumed. The mixture was filtered through a pad of Celite. The filtrate was concentrated to provide a viscous clear residue, II in 66.1 %. Material was clean enough to carry forward without purification. MS (ESI) mass calcd. for Ci0Hi8N2O2, 198.26; m/z found, 199.2 [M+H]+. 1H NMR (400 MHz, CDCI3) 4.73 - 4.50 (m, 1 H), 3.98 (t, J = 8.3, 1 H), 3.46 - 3.15 (m, 2H), 3.09 - 2.99 (m, 1 H), 2.93 - 2.82 (m, 1 H), 2.73 - 2.62 (m, 1 H), 2.53 - 2.42 (m, 1 H), 2.31 (s, 1 H), 1 .43 (s, 9H).

Molecular Weight:198.26
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:198.136827821
Monoisotopic Mass:198.136827821
Topological Polar Surface Area:41.6
Heavy Atom Count:14
Complexity:247
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes