Dipropylamine → HCID 70664992, compound

HRID 1403641Notes

Reaction equation

HRID 1403641 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:26][CH2:27][CH2:28][CH3:29])[CH2:24][CH3:25].CCN(C(C)C)C(C)C>CS(C)=O.O>[CH2:23]([N:26]([CH2:27][CH2:28][CH3:29])[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)[CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 81531DiisopropylethylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70664992HCID 70664992, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (100 mg, 0.32 mmol) in DMSO (3 mL) was added dipropylamine (100 mg, 0.99 mmol) and DIEA (100 mg, 0.77 mmol). The resulting solution was stirred overnight at 85° C. and then diluted with water (50 mL), extracted with ethyl acetate (3×20 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2.5%-4% ethyl acetate in petroleum ether) to afford methyl 3-(dipropylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (50 mg, 41%).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified via silica gel column chromatography (2.5%-4% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a88d25a5508f48e7ad2fcb75e2c2ce5b
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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