2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → 2-(4-(4-Fluorobenzoyl)piperidin-1-yl)-N-neopentyl-N-((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)acetamide

HRID 713485Notes

Reaction equation

HRID 713485 reaction equation
[CH2:1]([NH:6][CH2:7][C:8]1[NH:9][C:10](=[O:18])[C:11]2[CH2:17][O:16][CH2:15][CH2:14][C:12]=2[N:13]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].[F:19][C:20]1[CH:37]=[CH:36][C:23]([C:24]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33](O)=[O:34])[CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][C:33]([N:6]([CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[CH2:7][C:8]3[NH:9][C:10](=[O:18])[C:11]4[CH2:17][O:16][CH2:15][CH2:14][C:12]=4[N:13]=3)=[O:34])[CH2:30][CH2:31]2)=[O:25])=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 1366271902-((neopentylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one

Product 1

HCID 1362373362-(4-(4-Fluorobenzoyl)piperidin-1-yl)-N-neopentyl-N-((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)acetamideYield 17%

Procedure

The title compound (17 mg) was prepared following the general procedure of Example 1 from 2-((neopentylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (50 mg, 0.20 mmol) and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid (62 mg, 0.20 mmol). 1H NMR (400 MHz, CDC3) δ 7.98 (dd, J=9.0, 5.5 Hz, 2H), 7.07-7.21 (m, 2H), 4.61 (s, 2H), 4.49 (br. s., 2H), 3.86-4.05 (m, 2H), 3.30-3.50 (m, 3H), 3.13-3.29 (m, 2H), 2.90-3.13 (m, 2H), 2.52-2.76 (m, 4H), 2.01-2.27 (m, 3H), 1.88 (d, J=3.0 Hz, 1H), 1.02 (s, 3H), 0.96 (s, 7H). HRMS calculated for C27H35FN4O4 499.2721. found (ESI, [M+H]+), 499.2738. MS m/z 499.3 (M+1), retention time=3.32 min.

Sources & evidence

ORD record
ord-b1f216c27b6e45e58a3f6e4825c8bebc
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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