Hydrochloric Acid → HCID 44156858, compound

HRID 2389275Notes

Reaction equation

HRID 2389275 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[NH:12][CH2:11][CH2:10][N:9]2[CH2:15][C:16]2[CH:17]=[C:18]([C:27]([O:29]CC)=[O:28])[C:19](=[O:26])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:35].[Li+].[OH-].Cl>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13](=[O:14])[N:12]([CH3:35])[CH2:11][CH2:10][N:9]2[CH2:15][C:16]2[CH:17]=[C:18]([C:27]([OH:29])=[O:28])[C:19](=[O:26])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58256235HCID 58256235, compound

Product 1

HCID 44156858HCID 44156858, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of ethyl 1-{[2-(3-fluorophenyl)-3-oxopiperazin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate (0.050 g, 0.12 mmol) in 0.5 mL DMSO was added sodium hydride (6.1 mg, 0.15 mmol). After 15 minutes, iodomethane (0.010 mL, 0.15 mmol) was added and the reaction was stirred at room temperature for 15 hours. The mixture was then treated with saturated aqueous LiOH (0.3 mL). After 5 hours, 6 N HCl was added to pH ˜3, and the solution was purified by preparative reverse phase HPLC to afford the title compound that gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 409.9 for M+H+ [C22H2OPN3O4: 409.41]: 1H NMR (500 MHz, CD3OD) δ 9.37 (d, J=7.0 Hz, 1H), 8.37 (s, 1H), 7.93-7.89 (m, 2H), 7.60-7.56 (m, 1H), 7.28-7.25 (m, 1H), 7.15 (d, J=7.7 Hz, 1H), 7.08 (d, J=9.9 Hz, 1H), 7.00-6.95 (m, 1H), 4.16 (s, 1H), 3.88 (d, J=13.6 Hz, 1H), 3.77 (d, J=13.6 Hz, 1H), 3.67-3.60 (m, 1H), 3.34-3.31 (m, 1H), 3.10-3.06 (m, 1H), 2.97 (s, 3H), 2.78-2.71 (m, 1H).

Workup

  1. waitAfter 5 hours
  2. customthe solution was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-b96171ab04bb4ff495c5d1ab4e63d0de
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

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