2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → HCID 136237371, compound

HRID 713489Notes

Reaction equation

HRID 713489 reaction equation
[CH3:1][C@@H:2]([CH2:17][CH3:18])[CH2:3][NH:4][CH2:5][C:6]1[NH:7][C:8](=[O:16])[C:9]2[CH2:15][O:14][CH2:13][CH2:12][C:10]=2[N:11]=1.[F:19][C:20]1[CH:37]=[CH:36][C:23]([C:24]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33](O)=[O:34])[CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][C:33]([N:4]([CH2:3][C@@H:2]([CH3:1])[CH2:17][CH3:18])[CH2:5][C:6]3[NH:7][C:8](=[O:16])[C:9]4[CH2:15][O:14][CH2:13][CH2:12][C:10]=4[N:11]=3)=[O:34])[CH2:30][CH2:31]2)=[O:25])=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627230HCID 136627230, compound

Product 1

HCID 136237371HCID 136237371, compound

Procedure

Following the general procedure of Example 4, the title compound was prepared (38.2 mg) from (S)-2-((2-methylbutylamino)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 C27H35FN4O4 498.6. found 499.7 (ESI, M+H); 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.88-8.15 (m, 2H) 7.20 (t, J=8.59 Hz, 2H) 4.44-4.68 (m, 4H) 4.09-4.25 (m, 1H) 3.85-3.99 (m, 2H) 3.80 (d, J=11.12 Hz, 2H) 3.42 (d, J=7.58 Hz, 2H) 3.22-3.36 (m, 2H) 3.17 (br. s., 1H) 2.66-2.76 (m, 1H) 2.20 (br. s., 3H) 1.26-1.47 (m, 1H) 1.06-1.25 (m, 1H) 0.93 (ddd, J=6.82, 3.79, 3.54 Hz, 4H) 0.78-0.90 (m, 2H).

Sources & evidence

ORD record
ord-e5850bc1787f4b24a77f64866fd2be98
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…