Cyclobutylamine → HCID 70664990, compound

HRID 1403653Notes

Reaction equation

HRID 1403653 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.[CH:23]1([NH2:27])[CH2:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>CS(C)=O>[CH:23]1([NH:27][C:2]2[C:3]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70664990HCID 70664990, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (100 mg, 0.32 mmol) in DMSO (1 mL) in was added cyclobutanamine (100 mg, 1.41 mmol) and DIEA (110 mg, 0.85 mmol). The resulting solution was stirred for 2 hours at 70° C., and then quenched by the addition of water (50 mL) and extracted with dichloromethane (4×20 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (2%-10% ethyl acetate in petroleum ether) to afford methyl 3-(cyclobutylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (67 mg, 58%)

Workup

  1. customquenched by the addition of water (50 mL)
  2. extractionextracted with dichloromethane (4×20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified via silica gel column chromatography (2%-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d538f11085974ce1a2548ddea0f68c99
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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