2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid → 2-[4-(4-Methoxy-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

HRID 713513Notes

Reaction equation

HRID 713513 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[CH3:21][O:22][CH2:23][CH2:24][NH:25][CH2:26][C:27]1[NH:28][C:29](=[O:37])[C:30]2[CH2:36][O:35][CH2:34][CH2:33][C:31]=2[N:32]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([N:25]([CH2:24][CH2:23][O:22][CH3:21])[CH2:26][C:27]3[NH:28][C:29](=[O:37])[C:30]4[CH2:36][O:35][CH2:34][CH2:33][C:31]=4[N:32]=3)=[O:18])[CH2:13][CH2:14]2)=[O:8])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 712267662-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acidHCID 1366272422-[(2-Methoxy-ethylamino)-methyl]-3,5,7,8tetrahydro-pyrano[4,3-d]pyrimidin-4-one

Product 1

HCID 1362374352-[4-(4-Methoxy-benzoyl)-piperidin-1-yl]-N-(2-methoxy-ethyl)-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamideYield 23.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (22 mg, 0.044 mmol) was prepared following the general procedure of Example 1 from [4-(4-methoxy-benzoyl)-piperidin-1-yl]-acetic acid (65 mg, 0.188 mmol, 1.0 eq) and 2-[(2-methoxy-ethylamino)-methyl]-3,5,7,8tetrahydro-pyrano[4,3-d]pyrimidin-4-one (51.7 mg, 0.188 mmol, 1.0 eq). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.88-8.02 (m, 2H) 6.98-7.10 (m, 2H) 4.52 (br s, 1H) 4.36 (d, J=16.67 Hz, 3H) 3.75-3.92 (m, 5H) 3.52-3.58 (m, 3H) 3.42-3.45 (m, 3H) 3.27 (d, J=5.05 Hz, 15H) 3.17 (br s, 2H). HR-MS (m/z, MH+): 499.2580, 500.2607, 501.2628. HPLC retention time: 2.62 min (Ascentis 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-4a945b1cf2054cd4b2ae2fd99ff5380e
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…