Acetonitrile--water (1/1) → HCID 136237411, compound

HRID 713506Notes

Reaction equation

HRID 713506 reaction equation
[F:1][CH2:2][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: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.CC#N.O>C(O)=O>[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]([CH2:3][CH2:2][F:1])[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:32])[CH2:28][CH2:29]2)=[O:23])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627235HCID 136627235, compound

Product 1

HCID 136237411HCID 136237411, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Following the general procedure of Example 5, the title compound was prepared (0.09 g) from 2-((2-fluoroethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (0.18 g, 0.79 mmol, 1 eq.) and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid (0.19 g, 0.71 mmol, 0.9 eq.). 1H NMR (400 MHz, MeOD) δ ppm 8.04-8.18 (m, 2H), 7.26 (m, 2H), 4.71-4.80 (m, 1H), 4.60-4.67 (m, 1H), 4.59 (s, 2H), 4.48-4.53 (m, 1H), 4.46 (s, 1H), 4.37 (s, 2H), 3.89-3.96 (m, 2H), 3.83-3.90 (m, 1H), 3.77-3.84 (m, 1H), 3.66-3.78 (m, 3H), 3.46-3.61 (m, 1H), 3.16-3.28 (m, 1H), 2.49-2.73 (m, 2H), 1.91-2.25 (m, 4H). HRMS calculated for C24H29F2N4O4 475.2157. found (ESI, [M+H]+) 475.2178. MS (ESI) m/z 475.2 (M+H)+. Retention time: 4.08 min (5-95% CH3CN/H2O over 7.75 min with 0.1% formic acid, Inertsil ODS3 100×3 mm C18 column with flow rate of 1.0 m L/m in).

Sources & evidence

ORD record
ord-9827e6c0c9d941f7bad8289365a9e764
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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