Acetonitrile → 2-(4-Benzoyl-piperidin-1-yl)-N-(2-methoxy-ethyl)-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamide
Reaction equation
C1(C2[O:11][C:10]([CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=O)[CH2:14][CH2:13]3)=NN=2)C=CC=CC=1.[CH3:22][O:23][CH2:24][CH2:25][NH:26][CH2:27][C:28]1[NH:29][C:30](=[O:38])[C:31]2[CH2:37][O:36][CH2:35][CH2:34][C:32]=2[N:33]=1.[C:39](#N)[CH3:40]>>[C:10]([CH:12]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]([N:26]([CH2:25][CH2:24][O:23][CH3:22])[CH2:27][C:28]2[NH:29][C:30](=[O:38])[C:31]3[CH2:37][O:36][CH2:35][CH2:34][C:32]=3[N:33]=2)=[O:21])[CH2:16][CH2:17]1)(=[O:11])[C:40]1[CH:39]=[CH:14][CH:13]=[CH:12][CH:10]=1Participants
Reactant 3
Product 1
Procedure
The title compound (16.7 mg, 0.033 mmol) was prepared following the general procedure of Example 1 from [4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-piperidin-1-yl]-acetic acid (75 mg, 0.196 mmol, 1 eq) and 2-[(2-methoxy-ethylamino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (54.0 mg, 0.196 mmol, 1.0 eq). 1H NMR (400 MHz, chloroform-d) δ ppm 7.84-8.11 (m, 2H) 7.36-7.51 (m, 3H) 4.34-4.55 (m, 4H) 3.77-3.96 (m, 2H) 3.59-3.77 (m, 1H) 3.44-3.58 (m, 3H) 3.17-3.34 (m, 4H) 2.95 (dd, J=15.66, 12.13 Hz, 3H) 2.50-2.69 (m, 2H) 2.26-2.46 (m, 2H) 1.94-2.20 (m, 4H) 1.23-1.48 (m, 2H). HR-MS (m/z, MH+): 509.2519, 510.2566, 511.2614. HPLC retention time: 2.68 min (Agilent column 3.0×100 mm 3 um C18 column; flow rate of 1.0 mL/min with gradient from 5% to 95% acetonitrile in 10 min, 0.1% FA).
Sources & evidence
- ORD record
- ord-2627dd7cf2dc4e80a6c4d54ee08037b0
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181266B2
Reaction notes
Loading…