2-Bromo-1-cyclopropylethan-1-one → HCID 54109607, compound

HRID 1378781Notes

Reaction equation

HRID 1378781 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]3[CH:19]=[N:20][C:21]([C:22](=[S:24])[NH2:23])=[C:11]3[CH2:10]2)=[O:8])[CH2:3][CH2:2]1.[CH:25]1([C:28]([CH2:30]Br)=O)[CH2:27][CH2:26]1>C(O)C>[CH:25]1([C:28]2[N:23]=[C:22]([C:21]3[N:20]=[CH:19][N:12]4[C:13]5[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=5)[N:9]([C:7]([N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[O:8])[CH2:10][C:11]=34)[S:24][CH:30]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 109208412-Bromo-1-cyclopropylethan-1-oneHCID 22912939HCID 22912939, compound

Product 1

HCID 54109607HCID 54109607, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,5-dihydro-5-(morpholinocarbonyl)imidazo[1,5-a]quinoxaline-3-thiocarboxamide (0.29 g) and 1-bromomethyl cyclopropyl ketone (0.165 g) in ethanol (10 ml) is stirred at 20°-25° for 1 day and then at 80° for 5.5 hr, after which it stirred at 20°-25° for an additional 20 hr. The mixture is then concentrated under reduced pressure and chromatographed on silica gel eluting with methanol/dichloromethane (2/98). The product fractions are combined and rechromatographed using ethyl acetate/dichloromethane (25/75) to give a solid. Crystallization from dichloromethane/hexane gives the title compound; mp 193°-194°; MS (m/z) 407; IR (mineral oil) 1511, 1669, 1115, 1392, 1227 cm-1 ; NMR (CDCl3) 0.98, 2.09, 3.35, 3.66, 5.09, 6.79, 7.19, 7.28, 7.53, 8.01 δ.

Workup

  1. waitat 80° for 5.5 hr
  2. stirringafter which it stirred at 20°-25° for an additional 20 hr
  3. concentrationThe mixture is then concentrated under reduced pressure
  4. customchromatographed on silica gel eluting with methanol/dichloromethane (2/98)
  5. customrechromatographed
  6. customto give a solid
  7. customCrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-9888b7636dd3419195b720eed4cce361
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

Loading…