2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid → N-(Cyclopropylmethyl)-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 713479Notes

Reaction equation

HRID 713479 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.[CH:21]1([CH2:24][NH:25][CH2:26][C:27]2[NH:28][C:29](=[O:38])[C:30]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:31]=3[N:32]=2)[CH2:23][CH2:22]1>>[CH:21]1([CH2:24][N:25]([CH2:26][C:27]2[NH:28][C:29](=[O:38])[C:30]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:31]=3[N:32]=2)[C:16](=[O:18])[CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 712267662-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acidHCID 1366272142-((cyclopropylmethylamino)methyl)-6,7,8,9-tetrahydro-3H-cyclohepta[d]pyrimidin-4(5H)-one

Product 1

HCID 136237318N-(Cyclopropylmethyl)-2-(4-(4-methoxybenzoyl)piperidin-1-yl)-N-((4-oxo-4,5,6,7,8,9-hexahydro-3H-cyclohepta[d]pyrimidin-2-yl)methyl)acetamideYield 8%

Procedure

The title compound (18 mg, 8% yield) was prepared following the general procedures of Example 1 from 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid (124 mg, 0.45 mmol) and 2-((cyclopropylmethylamino)methyl)-6,7,8,9-tetrahydro-3H-cyclohepta[d]pyrimidin-4(5H)-one (104 mg, 0.45 mmol). 1H NMR (400 MHz, CDC3) δ 7.85 (d, J=8.5 Hz, 2H), 6.70-6.97 (m, 2H), 4.41 (s, 1H), 4.34 (s, 1H), 3.68-3.91 (m, 3H), 3.41 (s, 3H), 3.33 (d, J=7.0 Hz, 1H), 3.07-3.29 (m, 4H), 2.91 (d, J=10.5 Hz, 2H), 2.57-2.79 (m, 4H), 2.50 (br. s., 1H), 2.12-2.37 (m, 1H), 2.04 (d, J=14.1 Hz, 2H), 1.76 (d, J=5.0 Hz, 4H), 1.36-1.65 (m, 1H), 0.75-1.04 (m, 1H), 0.46 (d, J=7.5 Hz, 1H), 0.26-0.41 (m, 1H), 0.15-0.26 (m, 1H), 0.12 (d, J=4.5 Hz, 1H). HRMS calculated for C23H38N4O4 507.2971. found (ESI, [M+H]+), 507.2975. Retention time=3.54.

Sources & evidence

ORD record
ord-97a0f1b2b4c24d2997b78b9c83fd4b56
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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