2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → HCID 136237349, compound

HRID 713532Notes

Reaction equation

HRID 713532 reaction equation
[CH3:1][NH:2][CH:3]([C:5]1[NH:6][C:7](=[O:15])[C:8]2[CH2:14][O:13][CH2:12][CH2:11][C:9]=2[N:10]=1)[CH3:4].[F:16][C:17]1[CH:34]=[CH:33][C:20]([C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]([OH:32])=O)[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([CH:23]2[CH2:24][CH2:25][N:26]([CH2:29][C:30]([N:2]([CH3:1])[CH:3]([C:5]3[NH:6][C:7](=[O:15])[C:8]4[CH2:14][O:13][CH2:12][CH2:11][C:9]=4[N:10]=3)[CH3:4])=[O:32])[CH2:27][CH2:28]2)=[O:22])=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627260HCID 136627260, compound

Product 1

HCID 136237349HCID 136237349, compoundYield 24.8%

Procedure

The title compound (170 mg) was prepared according to the general procedure of Example 1 from 2-(1-(methylamino)ethyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (320 mg, 1.5 mmol) and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid (450 mg, 1.7 mmol). 1H NMR (400 MHz, CDC3) δ 12.88 (br. s., 1H), 7.97 (dd, J=8.8, 5.3 Hz, 2H), 7.05-7.21 (m, 2H), 4.48-4.70 (m, 2H), 3.95 (t, J=5.5 Hz, 2H), 3.68 (d, J=12.5 Hz, 1H), 3.39 (br. s., 1H), 3.16-3.36 (m, 1H), 3.07-3.16 (m, 1H), 2.83-3.07 (m, 3H), 2.62-2.77 (m, 5H), 2.56 (t, J=9.8 Hz, 1H), 2.27-2.47 (m, 1H), 1.97-2.27 (m, 2H), 1.76-1.94 (m, 1H), 1.46-1.69 (m, 3H). HRMS calculated for C24H23FN4O4 457.2251. found (ESI, [M+H]+), 457.2257. Retention time=1.83 min.

Sources & evidence

ORD record
ord-7b9c20e8403645a3a1a768ae6d0b03e9
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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