Triethylamine → HCID 57671748, compound

HRID 1038469Notes

Reaction equation

HRID 1038469 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([CH2:18]O)=[C:16]3[C:11]([NH:12][C:13]([CH3:22])([CH3:21])[C:14](=[O:20])[NH:15]3)=[CH:10][CH:9]=2)=[C:4]([O:23][CH3:24])[CH:3]=1.C(N(CC)CC)C.CS([Cl:36])(=O)=O.C(OCC)(=O)C>ClCCl.O1CCCC1.O>[Cl:36][CH2:18][C:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[O:23][CH3:24])=[CH:9][CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:20])[C:13]([CH3:22])([CH3:21])[NH:12]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 24780848HCID 24780848, compound

Product 1

HCID 57671748HCID 57671748, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-(4-Fluoro-2-methoxyphenyl)-8-hydroxymethyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 3-2, 70.0 mg, 0.21 mmol) was dissolved in the mixed solvent of anhydrous dichloromethane (1 mL) and anhydrous tetrahydrofuran (1.5 mL), and triethylamine (35 μL, 0.25 mmol) and methanesulfonyl chloride (18 μL, 0.23 mmol) were added thereto successively. The reaction mixture was stirred at room temperature overnight. Ethyl acetate (30 mL) and water (30 mL) were added to the reaction mixture and partitioned. The organic layer was washed with water (30 mL) and saturated brine (30 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 reference compound (49.5 mg) as a pale yellow solid. (Yield 68%)

Workup

  1. additionwere added
  2. custompartitioned
  3. washThe organic layer was washed with water (30 mL) and saturated brine (30 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0c7638701b1648c99456761dbc586180
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

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