Acetonitrile--water (1/1) → HCID 136237421, compound

HRID 713510Notes

Reaction equation

HRID 713510 reaction equation
[F:1][C:2]([F:18])([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:19][C:20]1[CH:37]=[CH:36][C:23]([C:24]([CH:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33](O)=[O:34])[CH2:28][CH2:27]2)=[O:25])=[CH:22][CH:21]=1.CC#N.O>C(O)=O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][C:33]([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)[CH2:3][C:2]([F:1])([F:17])[F:18])=[O:34])[CH2:30][CH2:31]2)=[O:25])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 18373917Acetonitrile--water (1/1)HCID 712264022-(4-(4-Fluorobenzoyl)piperidin-1-YL)acetic acidHCID 136627274HCID 136627274, compound

Product 1

HCID 136237421HCID 136237421, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Following the general procedure of Example 1, the title compound was prepared (0.015 g) from 2-((2,2,2-trifluoroethylamino)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 8.04-8.18 (m, 2H), 7.21-7.33 (m, 2H), 4.62-4.70 (m, 2H), 4.36-4.53 (m, 5H), 4.17-4.30 (m, 1H), 3.87-4.00 (m, 2H), 3.66-3.80 (m, 2H), 3.38-3.59 (m, 1H), 3.08-3.26 (m, 2H), 2.54-2.69 (m, 2H), 1.93-2.27 (m, 4H). HRMS calculated for C24H27F4N4O4 511.1968. found (ESI, [M+H]+) 511.1963. MS (ESI) m/z 511.2. (M+H)+. Retention time: 3.02 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-d75fd106e5c04dc8b8ef9b1379a4ce16
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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