Acetonitrile--water (1/1) → HCID 136237418, compound

HRID 713507Notes

Reaction equation

HRID 713507 reaction equation
[F:1][CH:2]([F:17])[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:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:31][C:32](O)=[O:33])[CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=1.CC#N.O>C(O)=O>[F:17][CH:2]([F:1])[CH2:3][N: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:32](=[O:33])[CH2:31][N:28]1[CH2:29][CH2:30][CH:25]([C:23](=[O:24])[C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:36][CH:35]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627267HCID 136627267, compound

Product 1

HCID 136237418HCID 136237418, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Following general procedure of Example 5, the title compound was prepared (0.046 g) from 2-((2,2-difluoroethylamino)methyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (0.18 g, 0.73 mmol, 1 eq.) and 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid (0.20 g, 0.73 mmol, 1 eq.). 1H NMR (400 MHz, MeOD) δ ppm 8.00-8.18 (m, 2H), 7.17-7.36 (m, 2H), 5.83-6.44 (m, 1H), 4.56-4.68 (m, 2H), 4.42-4.52 (m, 2H), 4.30-4.42 (m, 2H), 3.80-4.08 (m, 4H), 3.66-3.79 (m, 3H), 3.42-3.61 (m, 1H), 3.09-3.26 (m, 1H), 2.56-2.71 (m, 2H), 1.93-2.28 (m, 4H). HRMS calculated for C24H28F3N4O4 493.2063. found (ESI, [M+H]+) 493.2062. MS (ESI) m/z 493.2 (M+H)+. Retention time: 4.65 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-c7c454e7602a42d6b2e8466c1d9307db
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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