Diisopropylethylamine → HCID 89781847, compound

HRID 1056112Notes

Reaction equation

HRID 1056112 reaction equation
F[C:2]1[C:3]([CH3:15])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:7][CH:6]=2.CCN(C(C)C)C(C)C.Cl.[CH3:26][C:27]1([NH2:30])[CH2:29][CH2:28]1.C([O-])(O)=O.[Na+]>CS(C)=O>[CH3:15][C:3]1[C:2]([NH:30][C:27]2([CH3:26])[CH2:29][CH2:28]2)=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12](=[O:14])[CH3:13])[N:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 12953687(1-Methylcyclopropyl)amine hydrochlorideHCID 897818641-(3-Fluoro-2-methylquinoxalin-5-yl)ethanone

Product 1

HCID 89781847HCID 89781847, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

To a 250 mL round-bottomed flask was added 1-(3-fluoro-2-methylquinoxalin-5-yl)ethanone (126g) (14.5 g, 71 mmol), DMSO (100 mL), DIEA (27 mL, 156 mmol) and finally 1-methylcyclopropanamine hydrochloride (8.02 g, 92 mmol) (ChemBridge Corporation, San Diego, Calif.). The solution was heated at 85° C. for 7 h. After cooling to RT, the solution was poured into sat NaHCO3 (250 mL) and extracted with EtOAc (3×250 mL). The combined extracts were washed with H2O (3×250 mL) and brine and then dried (Na2SO4) and concentrated to afford 1-(2-methyl-3-((1-methylcyclopropyl)amino)-5-quinoxalinyl)ethanone (611a) as a purple solid, which was used directly in the subsequent step. m/z (ESI, +ve) 256.1 (M+H)+.

Workup

  1. temperatureAfter cooling to RT
  2. additionthe solution was poured
  3. extractionextracted with EtOAc (3×250 mL)
  4. washThe combined extracts were washed with H2O (3×250 mL) and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ee1526b501994188b82a1c9b466efbb3
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…