Hydrochloric Acid → HCID 44155103, compound

HRID 2389278Notes

Reaction equation

HRID 2389278 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[C:9]([C:18]([O:20]CC)=[O:19])[C:10](=[O:17])[N:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[OH-].[Na+].Cl>CN(C)C=O>[N:29]1([CH2:6][C:7]2[CH:8]=[C:9]([C:18]([OH:20])=[O:19])[C:10](=[O:17])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 86653285HCID 86653285, compound

Product 1

HCID 44155103HCID 44155103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 25 mL round bottom flask was charged with 0.75 mL of N,N-dimethylformamide, which was evacuated for 5 minutes and purged with nitrogen. To this flask was added ethyl 1-{[(methylsulfonyl)oxy]methyl}-4-oxo-4H-quinolizine-3-carboxylate, potassium carbonate (25 mg, 0.18 mmol), and then morpholine (0.016 mL, 0.18 mmol), which was stirred for 45 minutes. The reaction mixture was charged with 2.5 N NaOH (0.15 mL, 0.36 mmol), which was stirred for 16 hours. The mixture was acidified with 3 N HCl (1 mL) and then reduced in volume under vacuum, providing material, which was purified by reverse phase HPLC to yield the title compound that gave a proton NMR spectrum consistent with theory and a high resolution mass spectrum (ES+) m/z of 289.1205 calculated for M+H+ [C15H16N2O4: 289.1183]: 1H NMR (500 MHz, DMSO-d6) δ 13.76 (bs, CO2H), 9.81 (bs, 1H), 9.44 (s, 1H), 8.66 (m, 1H), 8.54 (m, 1H), 8.21 (m, 1H), 7.74 (t, J=6.8 Hz, 1H), 4.77 (s, 2H), 3.96 (m, 2H), 3.09-3.64 (m, 6H).

Workup

  1. customwas evacuated for 5 minutes
  2. custompurged with nitrogen
  3. customproviding material, which
  4. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-54ca604dc03a40d1a38f295415b0517c
Source dataset
uspto-grants-2012_09
Patent number
US08273737B2

Reaction notes

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