2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → HCID 136237374, compound

HRID 713492Notes

Reaction equation

HRID 713492 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][NH:7][CH2:8][C:9]1[NH:10][C:11](=[O:19])[C:12]2[CH2:18][O:17][CH2:16][CH2:15][C:13]=2[N:14]=1.[F:20][C:21]1[CH:38]=[CH:37][C:24]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34](O)=[O:35])[CH2:29][CH2:28]2)=[O:26])=[CH:23][CH:22]=1>>[F:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([CH:27]2[CH2:28][CH2:29][N:30]([CH2:33][C:34]([N:7]([CH2:8][C:9]3[NH:10][C:11](=[O:19])[C:12]4[CH2:18][O:17][CH2:16][CH2:15][C:13]=4[N:14]=3)[CH2:6][C@H:2]3[CH2:3][CH2:4][CH2:5][O:1]3)=[O:35])[CH2:31][CH2:32]2)=[O:26])=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627254HCID 136627254, compound

Product 1

HCID 136237374HCID 136237374, compound

Procedure

Following the general procedure of Example 4, the title compound was prepared (20.2 mg) from (R)-2-(((tetrahydrofuran-2-yl)methylamino)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 C27H33FN4O4 512.6. found 513.7 (ESI, M+H); 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.89 (dd, J=8.84, 5.31 Hz, 2H) 7.11 (t, J=8.59 Hz, 2H) 4.52-4.69 (m, 1H) 4.28-4.52 (m, 4H) 4.09-4.28 (m, 3H) 3.77-3.95 (m, 5H) 3.62-3.74 (m, 2H) 3.28-3.45 (m, 4H) 2.54-2.62 (m, 1H) 2.19 (d, J=7.07 Hz, 1H) 2.12 (br. s., 3H) 1.84-2.02 (m, 4H).

Sources & evidence

ORD record
ord-bb523980d44742bda35a1f983c998c26
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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