Hydrochloric Acid → HCID 178434497, compound

HRID 1792543Notes

Reaction equation

HRID 1792543 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:5][N:4](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:3]=1.[ClH:42].O1CCCC1.[OH-].[Na+]>O.C(OCC)(=O)C.CO>[ClH:42].[ClH:42].[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[C:10]3[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:5][NH:4][N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23537635HCID 23537635, compound

Product 1

HCID 178434497HCID 178434497, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 33 mg 6-(3-methyl-1-trityl-1H-pyrazolyl)-4-(2-pyridyl)quinoline obtained in Example 154, 0.48 mL of 5 N hydrochloric acid, 3 mL tetrahydrofuran, and 3 mL methanol was stirred overnight at room temperature. The reaction solution was cooled with iced water and basified with 5N aqueous sodium hydroxide, then ethyl acetate and water were added thereto, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, 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 19 mg of the title compound as yellow crystals.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in ethyl acetate
  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-af1ed52550ec4c7c9bccbce765ce14d9
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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