Dichloromethane → HCID 58574950, compound

HRID 1807881Notes

Reaction equation

HRID 1807881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=1[CH3:23])[N:19]1[C:24]([C@H:27]4[CH2:32][CH2:31][C@H:30](O)[CH2:29][CH2:28]4)=[N:25][CH:26]=[C:18]1[C:17](=[O:34])[NH:16]3)=[O:12])[CH2:6][CH2:5]2.ClCCl.C(N(S(F)(F)F)CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=1[CH3:23])[N:19]1[C:24]([CH:27]4[CH2:32][CH2:31][CH:30]=[CH:29][CH2:28]4)=[N:25][CH:26]=[C:18]1[C:17](=[O:34])[NH:16]3)=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 178421840HCID 178421840, compound

Product 1

HCID 58574950HCID 58574950, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixed solution of 87 mg of 7-[(5-chloro-2,3-dihydro-1H-indol -1-yl)carbonyl]-1-(trans-4-hydroxycyclohexyl)-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one and 2.8 mL of dichloromethane was cooled to −70° C., and 48 μL of N,N-diethylaminosulfur trifluoride was added thereto, followed by stirring at the same temperature for 2 hours. To the mixed reaction liquid were added a saturated aqueous sodium hydrogen carbonate solution and chloroform, followed by extraction with chloroform, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Then, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3). To the obtained solid was added 1.5 mL of methanol to give a mixture, and then warmed. A precipitate was collected by filtration and dried under reduced pressure to obtain 7 mg of 7-[(5-chloro-2,3-dihydro-1H-indol-1-yl)carbonyl]-1-(cyclohex-3-en-1-yl)-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one as a white solid.

Workup

  1. customTo the mixed reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThen, the solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3)
  7. additionTo the obtained solid was added 1.5 mL of methanol
  8. customto give a mixture
  9. temperaturewarmed
  10. filtrationA precipitate was collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-babcb77d69134f038fa91a005d12f77f
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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