1,4-Dioxane hydrochloride → 7-(4-Hydroxy-2-methoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871994

Reaction equation

HRID 871994 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9]COC)[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]([CH2:23][N:24]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[O:48][CH3:49])[C:25]([O:27][CH2:28][CH:29]2[C:41]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:35]3[C:30]2=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])=[C:21]2[C:16]([NH:17][C:18]([CH3:53])([CH3:52])[C:19](=[O:51])[N:20]2[CH3:50])=[CH:15][CH:14]=1.Cl.O1CCOCC1>O1CCOCC1.C(OCC)(=O)C>[OH:9][C:7]1[CH:6]=[CH:5][C:4]([C:13]2[C:22]([CH2:23][N:24]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[O:48][CH3:49])[C:25]([O:27][CH2:28][CH:29]3[C:41]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:35]4[C:30]3=[CH:31][CH:32]=[CH:33][CH:34]=4)=[O:26])=[C:21]3[C:16]([NH:17][C:18]([CH3:52])([CH3:53])[C:19](=[O:51])[N:20]3[CH3:50])=[CH:15][CH:14]=2)=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 583371967-(2-Methoxy-4-methoxymethoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 583372217-(4-Hydroxy-2-methoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 56%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

7-(2-Methoxy-4-methoxymethoxyphenyl)-8-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 12-1, 137 mg, 0.192 mmol) was dissolved in 1,4-dioxane (1 mL) and 4N hydrochloride/1,4-dioxane solution (144 μL, 0.576 mmol) was added thereto. After the reaction mixture was stirred at room temperature for 2 hours, the mixture was diluted with ethyl acetate (100 mL). The mixture was washed with water (100 mL) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (71.6 mg) as a colorless solid. (Yield 56%)

Workup

  1. washThe mixture was washed with water (100 mL) and saturated brine (50 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ba98da6075e24cd58b037269f671d355
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Linked notes

Loading…