Diisopropylethylamine → 8-(5-Fluoro-2-methylphenoxymethyl)-7-[2-methoxy-4-(3-methoxycarbonylbenzoyloxy)phenyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038500Notes

Reaction equation

HRID 1038500 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:34]([O:45][CH3:46])(=[O:44])[C:35]1[CH:43]=[CH:42][CH:41]=[C:37]([C:38]([O-])=[O:39])[CH:36]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[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]([O:29][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][CH:43]=[C:35]([C:34]([O:45][CH3:46])=[O:44])[CH:36]=3)=[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

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 69512791,3-Benzenedicarboxylic acid, monomethyl esterHCID 252112638-(5-Fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

Product 1

HCID 576717218-(5-Fluoro-2-methylphenoxymethyl)-7-[2-methoxy-4-(3-methoxycarbonylbenzoyloxy)phenyl]-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-(5-fluoro-2-methylphenoxymethyl)-7-(4-hydroxy-2-methoxyphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 11, 25.3 mg, 0.0562 mmol), monomethyl isophthalate (20.5 mg, 0.114 mmol), N,N-diisopropylethylamine (38.8 μL, 0.223 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (43.4 mg, 0.114 mmol) was dissolved in anhydrous N,N-dimethylformamide (0.5 mL) and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (15 mL). The mixture was washed with water (15 mL) and saturated saturated brine (15 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 (22.0 mg) as a colorless solid. (Yield 64%)

Workup

  1. washThe mixture was washed with water (15 mL) and saturated saturated brine (15 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-c88336af1f0c4bf699b3fd96a67b2c84
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

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