Dichloromethane → HCID 178434499, compound

HRID 1792544Notes

Reaction equation

HRID 1792544 reaction equation
[CH3:1][S:2]([C:5]1[S:9][C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[C:21]([CH3:44])=[N:22][N:23](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:24]=4)[CH:18]=3)[N:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].FC(F)(F)C(O)=O.[Cl:52]CCl.[OH-].[Na+]>O.C(OCC)(=O)C>[ClH:52].[CH3:44][C:21]1[C:20]([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[C:8]2[S:9][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:24][NH:23][N:22]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22032351HCID 22032351, compound

Product 1

HCID 178434499HCID 178434499, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 33 mg 4-[5-(methylsulfonyl)-2-thienyl]-6-(3-methyl-1-trityl-1H-4-pyrazolyl)quinoline obtained in Example 156, 0.5 mL trifluoroacetic acid and 2 mL dichloromethane was stirred overnight at room temperature. The reaction solution was cooled with iced water and basified with 5 N aqueous sodium hydroxide, then ethyl acetate and water were added thereto, and the organic layer was separated. The aqueous layer was saturated with common salt and then extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The residue was dissolved in methanol, and 0.15 mL of 4 N hydrochloric acid/ethyl acetate was added thereto. The reaction solution was evaporated, then ethyl acetate was added to the residue, and the formed crystals were separated by filtration to give 13 mg of the title compound as a pale yellow solid.

Workup

  1. customthe organic layer was separated
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in methanol
  7. addition0.15 mL of 4 N hydrochloric acid/ethyl acetate was added
  8. customThe reaction solution was evaporated
  9. additionethyl acetate was added to the residue
  10. customthe formed crystals were separated by filtration

Sources & evidence

ORD record
ord-edb59f1adaa647fa87ca9cb6a0dd350f
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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