2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → 2-(4-(4-Fluorobenzoyl)piperidin-1-yl)-N-(4-fluorobenzyl)-N-((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)acetamide
Reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][CH2:8][C:9]2[NH:10][C:11](=[O:19])[C:12]3[CH2:18][O:17][CH2:16][CH2:15][C:13]=3[N:14]=2)=[CH:4][CH:3]=1.[F:22][C:23]1[CH:40]=[CH:39][C:26]([C:27]([CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][C:36](O)=[O:37])[CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([CH:29]2[CH2:30][CH2:31][N:32]([CH2:35][C:36]([N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=3)[CH2:8][C:9]3[NH:10][C:11](=[O:19])[C:12]4[CH2:18][O:17][CH2:16][CH2:15][C:13]=4[N:14]=3)=[O:37])[CH2:33][CH2:34]2)=[O:28])=[CH:39][CH:40]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound (20 mg) was prepared following the general procedure of Example 1 from 2-((4-fluorobenzylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (80 mg, 0.28 mmol) and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid (86 mg, 0.28 mmol, 85% purity). 1H NMR (400 MHz, CDC3) δ 7.98 (dd, J=8.0, 5.5 Hz, 2H), 7.10-7.35 (m, 4H), 6.90-7.10 (m, 2H), 4.46-4.67 (m, 3.5H), 4.29 (s, 1.5H), 3.78-4.03 (m, 1H), 3.42 (br. s., 3H), 3.05 (t, J=11.5 Hz, 2H), 2.68 (t, J=5.3 Hz, 3H), 2.59 (t, J=5.5 Hz, 1H), 2.38 (br. s., 1H), 2.09-2.31 (m, 3H), 1.88 (br. s., 1H), 1.74-1.86 (m, 1H). HRMS calculated for C29H30F2N4O4 537.2331. found (ESI, [M+H]+), 537.2313. MS m/z 537.2 (M+1), retention time=3.25 min.
Sources & evidence
- ORD record
- ord-2c373c088fd0442d917076764b572bc4
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181266B2
Reaction notes
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