Hydrochloric Acid → HCID 21922669, compound

HRID 1244992Notes

Reaction equation

HRID 1244992 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[C:16]([C:37]3[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=3)=[C:17]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)[N:18]([Si](C(C)C)(C(C)C)C(C)C)[CH:19]=2)(O)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:43]>CO.O.O1CCOCC1>[ClH:43].[ClH:43].[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:17]2[NH:18][CH:19]=[C:15]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[C:16]=2[C:37]2[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21922808HCID 21922808, compound

Product 1

HCID 21922669HCID 21922669, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

249 mg (0.689 mmol) of 4-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in Example 9 above] were dissolved in a mixture of 2.5 ml of methanol and 2.5 ml of water, after which 2.43 ml (9.646 mmol) of a 4 N solution of hydrogen chloride in dioxane were added to the solution. The resulting mixture was heated under reflux for 11 hours, after which the reaction mixture was concentrated by evaporation under reduced pressure and the residual solid was washed with hot isopropanol to give 216 mg (yield 80%) of the title compound as a pale yellow powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 11 hours
  3. concentrationafter which the reaction mixture was concentrated by evaporation under reduced pressure
  4. washthe residual solid was washed with hot isopropanol

Sources & evidence

ORD record
ord-de077d8be9ae450cb9c42b8fc39c4a94
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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