Hydrochloric Acid → HCID 9815070, compound

HRID 1244997Notes

Reaction equation

HRID 1244997 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[C:15]2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:10]1)=O)(C)(C)C>O1CCOCC1.C(O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[CH:18][N:14]([CH:11]3[CH2:12][CH2:13][NH:9][CH2:10]3)[C:15]=2[C:26]2[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21922692HCID 21922692, compound

Product 1

HCID 9815070HCID 9815070, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

6.01 ml (24.05 mmol) of a 4N solution of hydrogen chloride in dioxane were added to a solution of 1.96 g (4.81 mmol) of (±)-1-[1-(t-butoxycarbonyl)pyrrolidin-3-yl]-3-(4-fluorophenyl)-2-(pyridin-4-yl)-1H-pyrrole [prepared as described in step 18(i) above] in 10 ml of ethanol. The resulting mixture was stirred at 50° C. for 30 minutes, after which the solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium hydrogencarbonate was added to the residue thus obtained, and then this was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure to give 1.29 g (yield 87%) of the title compound as a pale yellow powder.

Workup

  1. distillationafter which the solvent was distilled off under reduced pressure
  2. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  3. customthus obtained
  4. extractionthis was extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-f983aa6f5f454c368eb8885d73765c58
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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