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

HRID 713487Notes

Reaction equation

HRID 713487 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.[F:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32](O)=[O:33])[CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1>>[CH:1]1([CH2:4][N: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)[C:32](=[O:33])[CH2:31][N:28]2[CH2:29][CH2:30][CH:25]([C:23](=[O:24])[C:22]3[CH:21]=[CH:20][C:19]([F:18])=[CH:36][CH:35]=3)[CH2:26][CH2:27]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 1362440742-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one

Product 1

HCID 136237361N-Cyclopropylmethyl-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-N-(4-oxo-3,5,7,8-tetrahydro-4H-pyrano[4,3-d]pyrimidin-2-ylmethyl)-acetamide

Procedure

Following the general procedure of Example 4, the title compound was prepared (14.4 mg) from 2-[(Cyclopropylmethyl-amino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid. Exact mass calculated for C26H31FN4O4 482.55. found 483.3 (ESI, M+H); 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.98 (dd, J=8.59, 5.56 Hz, 2H) 7.19 (t, J=8.59 Hz, 2H) 4.65 (s, 1H) 4.58 (br. s., 1H) 4.41-4.55 (m, 2H) 4.26 (br. s., 1H) 4.18 (br. s., 2H) 3.85-3.98 (m, 3H) 3.30 (d, J=7.07 Hz, 1H) 3.22 (d, J=6.57 Hz, 2H) 2.70 (br. s., 1H) 2.64 (br. s., 1H) 2.22 (br. s., 4H) 0.97 (d, J=4.55 Hz, 1H) 0.61 (d, J=7.58 Hz, 1H) 0.42 (d, J=7.07 Hz, 1H) 0.26 (d, J=4.55 Hz, 1H) 0.13-0.22 (m, 1H).

Sources & evidence

ORD record
ord-9243dccb6baf4567b748dce7161523de
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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