Dichloromethane → HCID 58574950, compound

HRID 1189493Notes

Reaction equation

HRID 1189493 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 mixed solvent, and then warmed and washed. The 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 mixed solvent
  9. temperaturewarmed
  10. washwashed
  11. filtrationThe precipitate was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-f14dec6d175d40c69817ba1bc0f9cd56
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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