Ammonia → HCID 10171667, compound

HRID 896169Notes

Reaction equation

HRID 896169 reaction equation
C[O:2][C:3]([CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16](=[O:22])[CH2:15][CH2:14]3)[CH2:6]1)=O.[NH3:23]>CO>[CH3:21][N:17]1[C:18]2[C:13](=[CH:12][C:11]([N:7]3[CH2:6][C@H:5]([C:3]([NH2:23])=[O:2])[O:9][C:8]3=[O:10])=[CH:20][CH:19]=2)[CH2:14][CH2:15][C:16]1=[O:22]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 68489313HCID 68489313, compound

Product 1

HCID 10171667HCID 10171667, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 3-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-2-oxo-oxazolidine-5-carboxylic acid methyl ester (Step 4, 150 mg, 0.49 mmol) in MeOH (1 mL) is added 2.0 M NH3 in MeOH (1 mL, 2.0 mmol). The reaction mixture is then heated at 50-60° C. until all of the solid disappears. Solvent is removed and the residue is dissolved in 20% MeOH/CH2Cl2 and purified by silica gel chromatography (10% MeOH/CH2Cl2) to give the title compound as a white solid (120 mg, 84%), 1H NMR (300 MHz, DMSO) δ 7.85 (br s, 1H), 7.60 (br s, 1H), 7.45-7.08 (m, 3H), 5.01 (dd, 1H), 4.25 (t, 1H), 3.99 (dd, 1H), 3.23 (s, 3H), 2.86 (t, 2H), 2.50 (m, 2H); MS for C14H15N3O4 m/z 290.5 (M+H)+.

Workup

  1. customSolvent is removed
  2. dissolutionthe residue is dissolved in 20% MeOH/CH2Cl2
  3. custompurified by silica gel chromatography (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3caa9d8a6c024a8985ff473c812c03d9
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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