2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid → 2-(4-(4-Methoxybenzoyl)piperidin-1-yl)-N-((4-oxo-4,5,6,7,8,9-hexahydro-3H-cyclohepta[d]pyrimidin-2-yl)methyl)acetamide

HRID 713478Notes

Reaction equation

HRID 713478 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[NH2:21][CH2:22][C:23]1[NH:24][C:25](=[O:34])[C:26]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:27]=2[N:28]=1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:21][CH2:22][C:23]3[NH:24][C:25](=[O:34])[C:26]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:27]=4[N:28]=3)=[O:18])[CH2:13][CH2:14]2)=[O:8])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 712267662-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acidHCID 1359753712-(aminomethyl)-6,7,8,9-tetrahydro-3H-cyclohepta[d]pyrimidin-4(5H)-one

Product 1

HCID 1362373172-(4-(4-Methoxybenzoyl)piperidin-1-yl)-N-((4-oxo-4,5,6,7,8,9-hexahydro-3H-cyclohepta[d]pyrimidin-2-yl)methyl)acetamideYield 44%

Procedure

The title compound (89 mg, 44% yield) was prepared following the general procedure of Example 1 from 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid (124 mg, 0.45 mmol) and 2-(aminomethyl)-6,7,8,9-tetrahydro-3H-cyclohepta[d]pyrimidin-4(5H)-one (87 mg, 0.45 mmol). 1H NMR (400 MHz, CDC3) δ 11.36 (br. s., 1H), 8.01 (br. s., 1H), 7.83-7.89 (m, J=9.1 Hz, 2H), 6.85-6.91 (m, 2H), 4.30 (d, J=5.6 Hz, 2H), 3.81 (s, 3H), 3.12-3.29 (m, 1H), 2.97-3.12 (m, 2H), 2.92 (br. s., 2H), 2.55-2.83 (m, 4H), 2.30 (br. s., 2H), 1.67-1.94 (m, 6H), 1.40-1.67 (m, 4H). HRMS calculated for C23H32N4O4 453.2502. found (ESI, [M+H]+), 453.2509. Retention time=3.09.

Sources & evidence

ORD record
ord-24b3f7caef4343cab220761fc4192c27
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…