2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid → HCID 136237333, compound

HRID 713482Notes

Reaction equation

HRID 713482 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:32])[C:26]2[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:32])[C:26]4[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 136103112HCID 136103112, compound

Product 1

HCID 136237333HCID 136237333, compoundYield 21.1%

Procedure

The title compound (70 mg) was prepared following the general procedure of Example 1 from 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid (307 mg, 0.78 mmol, 70% purity) and 2-(aminomethyl)-6,7-dihydro-3H-cyclopenta[d]pyrimidin-4(5H)-one (128 mg, 0.78 mmol). 1H NMR (400 MHz, CDC3) δ 10.58 (br. s., 1H), 8.06 (br. s., 1H), 7.95 (d, J=9.1 Hz, 2H), 6.98 (d, J=9.1 Hz, 2H), 4.41 (d, J=6.1 Hz, 2H), 3.90 (s, 3H), 3.28 (br. s., 3H), 3.02 (br. s., 2H), 2.70-2.95 (m, 4H), 2.43 (br. s., 2H), 2.09 (dq, J=7.8, 7.7 Hz, 2H), 1.91 (br. s., 4H). HRMS calculated for C23H28N4O4 425.2189. found (ESI, [M+H]+), 425.2180. Retention time=4.65 min.

Sources & evidence

ORD record
ord-09aa8433ffe845fb8d966514996ada6f
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…