2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid → 2-(4-(4-Methoxybenzoyl)piperidin-1-yl)-N-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)methyl)acetamide

HRID 713481Notes

Reaction equation

HRID 713481 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:32][C:31](=[O:33])[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[N:24]=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:32][C:31](=[O:33])[C:30]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=4[N:24]=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 1361031112-(Aminomethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one

Product 1

HCID 1362373202-(4-(4-Methoxybenzoyl)piperidin-1-yl)-N-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)methyl)acetamideYield 34%

Procedure

The title compound (100 mg) was prepared following the general procedure of Example 1 from 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid (265 mg, 0.67 mmol, 70% purity) and 2-(aminomethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one (120 mg, 0.67 mmol). 1H NMR (400 MHz, CDC3) δ 10.91 (br. s., 1H), 7.91 (br. s., 1H), 7.82-7.89 (m, 2H), 6.85-6.91 (m, J=8.6 Hz, 2H), 4.29 (d, J=6.1 Hz, 2H), 3.81 (s, 3H), 3.17 (d, J=6.6 Hz, 1H), 3.07 (br. s., 2H), 2.90 (br. s., 2H), 2.52 (t, J=6.1 Hz, 2H), 2.42 (t, J=6.1 Hz, 4H), 1.80 (br. s., 4H), 1.48-1.77 (m, 4H). HRMS calculated for C24H30N4O4 439.2345. found (ESI, [M+H]+), 439.2352. Retention time=2.84 min.

Sources & evidence

ORD record
ord-83d24722bd9c46ec9d213a6935e9f6c9
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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