Isopropylamine → HCID 70665294, compound

HRID 1403565Notes

Reaction equation

HRID 1403565 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.CC[N:25](C(C)C)[CH:26]([CH3:28])[CH3:27].CC(N)C>CS(C)=O.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([NH:25][CH:26]([CH3:28])[CH3:27])=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 70665294HCID 70665294, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (200 mg, 0.63 mmol) in DMSO (10 mL) was added DIEA (489 mg, 3.79 mmol) and propan-2-amine (149.4 mg, 2.53 mmol) under nitrogen atmosphere. After stirring overnight at 70° C., the reaction mixture was dissolved in water (100 mL), extracted with dichloromethane (3×80 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue. Purification via silica gel column chromatography (2% ethyl acetate in petroleum ether) afforded methyl 2-(4-fluorophenyl)-3-(isopropylamino)quinoxaline-6-carboxylate as a light yellow solid (100 mg, 44%).

Workup

  1. extractionextracted with dichloromethane (3×80 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a residue
  5. customPurification via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9eb24a6f6cff4f9b94eaecc9ac9f85e1
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…