2-(4-(4-Ethoxybenzoyl)piperidin-1-yl)acetic acid → 2-(4-(4-Ethoxybenzoyl)piperidin-1-yl)-N-((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)acetamide
Reaction equation
[NH2:1][CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH2:12][O:11][CH2:10][CH2:9][C:7]=2[N:8]=1.[CH2:14]([O:16][C:17]1[CH:34]=[CH:33][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30](O)=[O:31])[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1)[CH3:15]>>[CH2:14]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]([NH:1][CH2:2][C:3]3[NH:4][C:5](=[O:13])[C:6]4[CH2:12][O:11][CH2:10][CH2:9][C:7]=4[N:8]=3)=[O:31])[CH2:25][CH2:24]2)=[O:22])=[CH:33][CH:34]=1)[CH3:15]Participants
3
Procedure
The title compound (150 mg) was prepared following the general procedure of Example 1 from 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (300 mg, 1.66 mmol) and 2-(4-(4-ethoxybenzoyl)piperidin-1-yl)acetic acid (603 mg, 1.66 mmol). 1H NMR (400 MHz, CDC3) δ 10.67 (s, 1H), 8.07 (t, J=6.0 Hz, 1H), 7.92 (d, J=9.0 Hz, 2H), 6.94 (t, J=9.0 Hz, 2H), 4.56 (s, 2H), 4.37 (d, J=6.0 Hz, 2H), 4.10 (q, J=7.0 Hz, 2H), 3.95 (t, J=5.5 Hz, 2H), 3.20-3.29 (m, 1H), 2.91-3.00 (m, 2H), 2.66-2.72 (m, 2H), 2.30-2.40 (m, 2H), 1.80-1.90 (m, 4H), 1.45 (t, J=7.0 Hz, 3H). HRMS calculated for C24H30N4O5 455.2294. found (ESI, [M+H]+), 455.2308. MS m/z 455.2 (M+1), retention time=2.70 min.
Sources & evidence
- ORD record
- ord-ee420ede4adf449ba7e118559ca4486d
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181266B2
Reaction notes
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