Triethylamine → 7-[4-(3-Chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-8-(5-fluoro-2-methylphenoxymethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871998Notes

Reaction equation

HRID 871998 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:33])=[C:6]([CH:32]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2[O:30][CH3:31])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2.C(N(CC)CC)C.[Cl:41][C:42]1[CH:43]=[C:44]([N:48]=[C:49]=[O:50])[CH:45]=[CH:46][CH:47]=1>ClCCl>[Cl:41][C:42]1[CH:43]=[C:44]([NH:48][C:49]([O:29][C:26]2[CH:27]=[CH:28][C:23]([C:10]3[C:9]([CH2:8][O:7][C:6]4[CH:32]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[CH3:33])=[C:18]4[C:13]([NH:14][C:15]([CH3:22])([CH3:21])[C:16](=[O:20])[N:17]4[CH3:19])=[CH:12][CH:11]=3)=[C:24]([O:30][CH3:31])[CH:25]=2)=[O:50])[CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 252112638-(5-Fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576719547-[4-(3-Chlorophenylaminocarbonyloxy)-2-methoxyphenyl]-8-(5-fluoro-2-methylphenoxymethyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-(5-Fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 11, 20.3 mg, 0.0451 mmol) was dissolved in anhydrous dichloromethane (0.5 mL), then triethylamine (13.6 μL, 0.0977 mmol) and 3-chlorophenyl isocyanate (6 μL, 0.05 mmol) were added to the mixture successively. After the reaction mixture was stirred for 1 hour at room temperature, the mixture was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (22.4 mg) as a colorless solid. (Yield 82%)

Workup

  1. customthe mixture was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-afdb684e5bbd474aa47c88dca4af9096
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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