Dichloromethane → HCID 58575461, compound

HRID 1189481Notes

Reaction equation

HRID 1189481 reaction equation
[CH:1]1([C:6]2[N:10]3[C:11]4[C:16]([NH:17][C:18](=[O:19])[C:9]3=[CH:8][N:7]=2)=[CH:15][C:14]([C:20]([OH:22])=O)=[C:13]([CH3:23])[CH:12]=4)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:27]([CH:30]([CH3:32])[CH3:31])[CH2:28][CH3:29])(C)C.ClCCl.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1C[CH2:48][CH2:47][CH2:46]1>O>[CH:1]1([C:6]2[N:10]3[C:11]4[C:16]([NH:17][C:18](=[O:19])[C:9]3=[CH:8][N:7]=2)=[CH:15][C:14]([C:20]([N:27]2[C:30]3[C:31](=[CH:46][CH:47]=[CH:48][CH:32]=3)[CH2:29][CH2:28]2)=[O:22])=[C:13]([CH3:23])[CH:12]=4)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 58575441HCID 58575441, compound

Product 1

HCID 58575461HCID 58575461, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 90 mg of 1-cyclopentyl-8-methyl-4-oxo-4,5-dihydroimidazo[1,5-a]quinoxaline-7-carboxylic acid, 0.18 mL of diisopropylethylamine, and 5.4 mL of dichloromethane was added 162 mg of bromo(tripyrrolidin-1-yl)phosphonium hexafluorophosphate, followed by stirring at room temperature overnight. To the reaction liquid was added water, followed by extraction with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3). The obtained solid was heated and washed with 3 mL of ethyl acetate and 15 mL of normal hexane to obtain 183 mg of 1-cyclopentyl-7-(2,3-dihydro-1H-indol-1-ylcarbonyl)-8-methylimidazo[1,5-a]quinoxalin-4(5H)-one as a white solid.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3)
  7. temperatureThe obtained solid was heated
  8. washwashed with 3 mL of ethyl acetate and 15 mL of normal hexane

Sources & evidence

ORD record
ord-4b8c29a17516469ab808cb7780b37f16
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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