Triethylamine → HCID 67428596, compound

HRID 490139Notes

Reaction equation

HRID 490139 reaction equation
C(N(CC)CC)C.Cl[C:9]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[NH:11][C:10]1=[O:19].[CH2:28]([NH:30][C:31](=[O:38])[C@@H:32]1[CH2:36][CH:35]([F:37])[CH2:34][NH:33]1)[CH3:29].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:19])[C:9]2([N:33]1[CH2:34][CH:35]([F:37])[CH2:36][C@H:32]1[C:31]([NH:30][CH2:28][CH3:29])=[O:38])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 219059133,5-Dichloro-3-(2-methoxyphenyl)indolin-2-oneHCID 45115932HCID 45115932, compound

Product 1

HCID 67428596HCID 67428596, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.0 mL of triethylamine was added under ice cooling to a 15 mL chloroform solution of 1.02 g of 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one and 530 mg of the compound obtained in step 8-2, after which the reaction mixture was stirred for 18.5 hours at room temperature. 20 mL of a 5% potassium carbonate aqueous solution was poured into the reaction solution under stirring, and extraction was performed with chloroform (20 mL×2). The combined organic layer was washed with saturated brine and dried with sodium sulfate, then the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was separated and purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone=98/2; v/v) to obtain two kinds of diastereoisomer of the titled compound in amounts of 708 mg (isomer A: colorless, amorphous) and 501 mg (isomer B: colorless, amorphous).

Workup

  1. stirringunder stirring
  2. extractionextraction
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried with sodium sulfate
  5. filtrationthe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customwas separated
  9. custompurified by column chromatography (silica gel 60, mobile phase: ethyl acetate/acetone=98/2; v/v)

Sources & evidence

ORD record
ord-91438946938f4d7f8953e2fd638cd769
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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