2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid → HCID 136237334, compound

HRID 713483Notes

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:28][C:27](=[O:29])[C:26]([CH3:30])=[C:25]([CH3:31])[N:24]=1>>[CH3:31][C:25]1[N:24]=[C:23]([CH2:22][NH:21][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)[NH:28][C:27](=[O:29])[C:26]=1[CH3:30]

Participants

Reactant 2

HCID 712267662-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid

HCID 136103101HCID 136103101, compound

Product 1

HCID 136237334HCID 136237334, compoundYield 49.3%

Procedure

The title compound (183 mg) was prepared following the general procedure of Example 1 from 2-(4-(4-methoxybenzoyl)piperidin-1-yl)acetic acid (357 mg, 0.90 mmol, 70% purity) and 2-(aminomethyl)-5,6-dimethylpyrimidin-4(3H)-one (138 mg, 0.90 mmol). 1H NMR (400 MHz, DMSO-d6) δ 12.21 (br. s., 1H), 8.20 (s, 1H), 7.96 (d, J=9.1 Hz, 2H), 7.02-7.06 (m, 2H), 4.14 (d, J=5.6 Hz, 2H), 3.84 (s, 3H), 2.86-3.08 (m, 4H), 2.25-2.39 (m, 2H), 2.22 (s, 1H), 2.16 (s, 3H), 1.88 (s, 3H), 1.63-1.82 (m, 4H). HRMS calculated for C22H28N4O4 413.2189. found (ESI, [M+H]+), 413.2195. Retention time=4.44 min.

Sources & evidence

ORD record: ord-2ccfa928304f4a24acb38b0fa385da42
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181266B2

Reaction notes

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