N-Methylbenzylamine → HCID 70665335, compound

HRID 1403626Notes

Reaction equation

HRID 1403626 reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH2:23]([NH:30][CH3:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>CS(C)=O>[CH2:23]([N:30]([CH3:31])[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70665335HCID 70665335, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.63 mmol) in DMSO (4 mL) was added benzyl(methyl)amine (92 mg, 0.76 mmol), and DIEA (163 mg, 1.26 mmol). The resulting solution was stirred for 2 hours at 85° C. Then the mixture was quenched of water (100 mL) and extracted with dichloromethane (3×50 mL) The organic layers were combined and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 3-[benzyl(methyl)amino]-2-(4-fluorophenyl)quinoxaline-6-carboxylate as yellow oil (100 mg, 39%).

Workup

  1. customThen the mixture was quenched of water (100 mL)
  2. extractionextracted with dichloromethane (3×50 mL) The organic layers
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-337a51de68c542bfa0a52da2c931534f
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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