2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → HCID 136237384, compound

HRID 713494Notes

Reaction equation

[C@H:1]([NH:5][CH2:6][C:7]1[NH:8][C:9](=[O:17])[C:10]2[CH2:16][O:15][CH2:14][CH2:13][C:11]=2[N:12]=1)([CH2:3][CH3:4])[CH3:2].[F:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32](O)=[O:33])[CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1>>[C@H:1]([N:5]([CH2:6][C:7]1[NH:8][C:9](=[O:17])[C:10]2[CH2:16][O:15][CH2:14][CH2:13][C:11]=2[N:12]=1)[C:32](=[O:33])[CH2:31][N:28]1[CH2:29][CH2:30][CH:25]([C:23](=[O:24])[C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:36][CH:35]=2)[CH2:26][CH2:27]1)([CH2:3][CH3:4])[CH3:2]

Participants

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid

HCID 136627237HCID 136627237, compound

Product 1

HCID 136237384HCID 136237384, compound

Procedure

Following general procedure of Example 4, the title compound was prepared (11 mg) from (R)-2-((sec-butylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid. Exact mass calculated for C26H33FN4O4 484.6. found 485.4 (ESI, M+H); 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.87-8.07 (m, 2H) 7.16 (t, J=8.59 Hz, 2H) 4.41-4.58 (m, 2H) 4.19-4.41 (m, 3H) 4.13 (d, J=7.07 Hz, 1H) 3.82-3.99 (m, 2H) 3.34 (br. s., 2H) 3.25 (br. s., 1H) 3.13 (br. s., 1H) 2.87-3.07 (m, 1H) 2.55-2.69 (m, 2H) 2.25 (br. s., 2H) 1.98 (br. s., 1H) 1.88 (br. s., 2H) 1.72 (br. s., 1H) 1.16-1.28 (m, 3H) 1.09 (d, J=6.57 Hz, 1H) 0.69-0.89 (m, 3H).

Sources & evidence

ORD record: ord-6b443d6d832b4dd092a134c372412456
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181266B2

Reaction notes

Loading…