4-(2-AMINOETHYL)TETRAHYDROPYRAN

Clear colorless liquid

(Tetrahydro-4-pyranyl) -acetonitrile (75 g, 0.60 mol), Pd / C 2.5 g, 400 ml of ethanol was added to a hydrogenation vessel, Replacement 3 times, Hydrogenation, Keep the pressure IMPa, Temperature 25 ° C, Stirring reaction 12h, The reaction was filtered and the filtrate was transferred to the reactionAnd distilled under reduced pressure to give 65.8 g (0.5 lmo 1) of 4- (2-aminoethyl) tetrahydropyran oil.A mixture of 2- (5-amino-2- (furan-2-yl) -7H-pyrazolo [4, 3-e] [1, 2, 4] triazolo [1, 5-c] pyrimidin-7-yl) -2-phenylpropanoic acid (100 mg, 0.2570 mmol) , 2- (tetrahydro-2H-pyran-4- yl) ethan-1-amine (40 mg, 0.3085 mmol) , HATU (146 mg, 0.3856 mmol) , DIPEA (99 mg, 0.7712 mmol) in DMF (3 mL) was stirred at rt for 3 hours. The reaction mixture was poured into H 2O (10 mL) and extracted with EtOAc (15 mL x 3) . The combined organic layers were washed with brine, dried over Na 2SO 4, concentrated and purified by column chromatography (DCM/MeOH=40: 110: 1) to give the product (62 mg, 48.2%) . 1HNMR (400 MHz, DMSO-d6) delta 8.24 (s, 1H) , 8.00 (s, 2H) , 7.95 (d, J = 0.9 Hz, 1H) , 7.53 (t, J = 5.6 Hz, 1H) , 7.34 -7.20 (m, 4H) , 7.15 (dd, J = 8.0, 1.4 Hz, 2H) , 6.74 (dd, J = 3.4, 1.8 Hz, 1H) , 3.76 -3.66 (m, 2H) , 3.15 (q, J = 6.6 Hz, 2H) , 3.04 (dd, J = 23.4, 11.6 Hz, 2H) , 2.28 (s, 3H) , 1.51 -1.39 (m, 2H) , 1.37 -1.27 (m, 2H) , 1.26 -1.17 (m, 1H) , 1.02 (ddd, J = 23.9, 12.0, 4.2 Hz, 2H) . MS: M/e 501 (M+1) +. (0.5 mmol) and methyl 2-(2-(chloromethyl)phenyl)acetate (0.5 mmol) were mixed in 5ml of DMF; DIPEA (0.75 mmol) was added. The mixture was heated at 80 C for 5 h, cooled; solvent was removed by evaporation and residue was purified by HPLC. Yield: 41%. 1H NMR (400 MHz, Chloroform-d) d 7.62 (ddt, J = 16.3, 11.9, 5.3 Hz, 3H), 4.87 (s, 2H), 4.27 - 4.18 (m, 2H), 3.88 (d, J = 8.7 Hz, 4H), 3.66 (td, J = 11.7, 2.0 Hz, 2H), 3.56 (s, 2H), 2.91 (dd, J = 3.8, 1.9 Hz, 1H), 2.05 (d, J = 12.9 Hz, 2H), 1.88 (t, J = 6.4 Hz, 3H), 1.68 - 1.57 (m, 2H). m/z=260.2Benzyl N-(2-tetrahydropyran-4-ylethyl)carbamate Benzyl chloroformate (0.54 ml_, 640 mg, 3.8 mmol) was added slowly to a solution of

Molecular Weight:129.20
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:129.115364102
Monoisotopic Mass:129.115364102
Topological Polar Surface Area:35.2
Heavy Atom Count:9
Complexity:69.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes