[4-(4-But-2-ynyloxy-benzoyl)-piperidin-1-yl]-acetic acid → 2-[4-(4-But-2-ynyloxy-benzoyl)-piperidin-1-yl]-N-cyclopropylmethyl-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamide
Reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][C:7]2[NH:8][C:9](=[O:17])[C:10]3[CH2:16][O:15][CH2:14][CH2:13][C:11]=3[N:12]=2)[CH2:3][CH2:2]1.[CH2:18]([O: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)[C:19]#[C:20][CH3:21]>>[CH2:18]([O: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]([N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[CH2:6][C:7]3[NH:8][C:9](=[O:17])[C:10]4[CH2:16][O:15][CH2:14][CH2:13][C:11]=4[N:12]=3)=[O:37])[CH2:31][CH2:30]2)=[O:28])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]Participants
Reactant 2
Product 1
Procedure
The title compound (90 mg) was prepared following the general procedure of Example 1 from 2-[(cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (140 mg, 0.59 mmol) and [4-(4-but-2-ynyloxy-benzoyl)-piperidin-1-yl]-acetic acid (187 mg, 0.59 mmol). 1H NMR (400 MHz, MeOD) δ: 8.01 (d, J=8.6 Hz, 2H), 7.08 (d, J=9.1 Hz, 2H), 4.79-4.76 (m, 2H), 4.66 (s, 1H), 4.57 (s, 1H), 4.50-4.45 (m, 2H), 4.39 (s, 2H), 3.92 (t, J=5.6 Hz, 2H), 3.80-3.67 (m, 2H), 3.36 (d, J=7.1 Hz, 2H), 3.33-3.28 (m, 6H), 2.69-2.58 (m, 2H), 2.22-2.02 (m, 4H), 1.83 (t, J=2.5 Hz, 3H), 1.11-0.89 (m, 1H), 0.66-0.43 (m, 2H), 0.34-0.19 (m, 2H). HRMS calculated for C33H38N4O3=533.2764. found (ESI, [M+H]+), 533.2788. LRMS m/z: ES+=533.7 (M+H), retention time 1.08.
Sources & evidence
- ORD record
- ord-c79aeee6a71d47d5ac9f6897310245f2
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181266B2
Reaction notes
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