Acetonitrile--water (1/1) → HCID 136237422, compound

HRID 713511Notes

Reaction equation

HRID 713511 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH:8][CH2:9][C:10]1[NH:11][C:12](=[O:20])[C:13]2[CH2:19][O:18][CH2:17][CH2:16][C:14]=2[N:15]=1)[CH3:7].[F:21][C:22]1[CH:39]=[CH:38][C:25]([C:26]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35](O)=[O:36])[CH2:30][CH2:29]2)=[O:27])=[CH:24][CH:23]=1.CC#N.O>C(O)=O>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([CH:28]2[CH2:29][CH2:30][N:31]([CH2:34][C:35]([N:8]([CH2:9][C:10]3[NH:11][C:12](=[O:20])[C:13]4[CH2:19][O:18][CH2:17][CH2:16][C:14]=4[N:15]=3)[CH:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH3:7])=[O:36])[CH2:32][CH2:33]2)=[O:27])=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627269HCID 136627269, compound

Product 1

HCID 136237422HCID 136237422, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Following the general procedure of Example 1, the title compound was prepared (0.02 g) from 2-((1-(thiophen-2-yl)ethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid. 1H NMR (400 MHz, MeOD) δ ppm 8.04-8.17 (m, 2H), 7.22-7.46 (m, 3H), 6.99-7.17 (m, 1H), 6.86-6.95 (m, 1H), 6.09-6.24 (m, 1H), 5.36-5.47 (m, 1H), 4.24-4.64 (m, 6H), 3.85-3.95 (m, 2H), 3.69-3.83 (m, 2H), 3.38-3.64 (m, 1H), 3.11-3.27 (m, 1H), 2.49-2.68 (m, 2H), 1.99-2.26 (m, 4H), 1.74-1.85 (m, 1H), 1.55 (d, J=7.03 Hz, 2H). HRMS calculated for C29H31F1N4O4S1 539.2128. found (ESI, [M+H]+) 539.2128. MS (ESI) m/z 539.2. (M+H)+. Retention time: 3.21 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 mL/min).

Sources & evidence

ORD record
ord-14ee565c2b254794a32305aa60dd76eb
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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