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

HRID 713480Notes

Reaction equation

HRID 713480 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:36][C:35](=[O:37])[C:34]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[N:28]=2)[CH2:23][CH2:22]1>>[CH:21]1([CH2:24][N:25]([CH2:26][C:27]2[NH:36][C:35](=[O:37])[C:34]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[N:28]=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 1366272512-[(cyclopropylmethyl-amino)-methyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one

Product 1

HCID 136237319N-(Cyclopropylmethyl)-2-(4-(4-methoxybenzoyl)piperidin-1-yl)-N-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)methyl)acetamideYield 1%

Procedure

The title compound (26 mg, 1% yield) was prepared following the general procedure of Example 7 from 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid and 2-[(cyclopropylmethyl-amino)-methyl]-5,6,7,8-tetrahydro-3H-quinazolin-4-one. 1H NMR (400 MHz, CD3OD) δ 7.75-7.83 (m, J=9.1 Hz, 2H), 6.77-6.88 (m, J=9.1 Hz, 2H), 4.48 (s, 1H), 4.26-4.44 (m, 1H), 4.04-4.26 (m, 2H), 3.67 (s, 3H), 3.37-3.59 (m, 2H), 2.93-3.19 (m, 5H), 2.39 (t, J=5.6 Hz, 2H), 2.22 (t, J=5.8 Hz, 2H), 1.91 (br. s., 3H), 1.75-1.86 (m, 1H), 1.47-1.75 (m, 4H), 0.65-0.90 (m, 1H), 0.40 (q, J=6.1 Hz, 1H), 0.16-0.32 (m, 1H), 0.06-0.16 (m, 1H), −0.13-0.06 (m, 1H). HRMS calculated for C28H36N4O4 493.2815. found (ESI, [M+H]+), 493.2826. Retention time=3.50 min.

Sources & evidence

ORD record
ord-ed41dc47402249bab843738ca0575fc3
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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