2-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acid → HCID 136237373, compound

HRID 713491Notes

Reaction equation

HRID 713491 reaction equation
[CH2:1]([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)[C:2]#[CH:3].[F:17][C:18]1[CH:35]=[CH:34][C:21]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([CH2:30][C:31](O)=[O:32])[CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([CH:24]2[CH2:25][CH2:26][N:27]([CH2:30][C:31]([N:4]([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)[CH2:1][C:2]#[CH:3])=[O:32])[CH2:28][CH2:29]2)=[O:23])=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627259HCID 136627259, compound

Product 1

HCID 136237373HCID 136237373, compound

Procedure

Following the general procedure of Example 4, the title compound was prepared (44.3 mg) from 2-((prop-2-ynylamino)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 C25H27FN4O4 466.5. found 467.7 (ESI, M+H); 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.98 (dd, J=9.09, 5.56 Hz, 2H) 7.20 (t, J=8.59 Hz, 2H) 4.67 (d, J=9.60 Hz, 2H) 4.51 (d, J=15.16 Hz, 2H) 4.26-4.41 (m, 3H) 4.22 (br. s., 2H) 3.88-4.01 (m, 4H) 2.63-2.85 (m, 2H) 2.32 (br. s., 1H) 2.24 (br. s., 4H) 1.46-1.58 (s, 2H).

Sources & evidence

ORD record
ord-e0432cc49c714ea6a326dd747c344a0a
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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