Hydrochloric Acid → HCID 71599697, compound

HRID 2167775Notes

Reaction equation

HRID 2167775 reaction equation
Cl.C(OC([NH:9][C:10]1([C:40]([O:42][CH3:43])=[O:41])[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:19]=[N:20][N:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:31][CH2:30][CH2:29][C@@H:28]4[C:32]4[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=4[F:39])=[CH:23][C:22]=23)=[O:17])[CH2:12][CH2:11]1)=O)(C)(C)C>O1CCOCC1.O>[NH2:9][C:10]1([C:40]([O:42][CH3:43])=[O:41])[CH2:11][CH2:12][N:13]([C:16]([C:18]2[CH:19]=[N:20][N:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:31][CH2:30][CH2:29][C@@H:28]4[C:32]4[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=4[F:39])=[CH:23][C:22]=23)=[O:17])[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89618779HCID 89618779, compound

Product 1

HCID 71599697HCID 71599697, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
27.5 °C

Procedure

A mixture of 4M HCl solution in Dioxane (1 mL) and (R)-methyl 4-((tert-butoxycarbonyl)amino)-1-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carbonyl)piperidine-4-carboxylate (50 g, 0.085 mmol) was stirred at 20-35° C. for 3 h. After which the reaction mixture was concentrated under reduced pressure to afford the crude. The residue obtained was dissolved in water, extracted with ethylacetate, washed with saturated NaHCO3 solution followed by brine and dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford 15 mg of the title compound.

Workup

  1. concentrationAfter which the reaction mixture was concentrated under reduced pressure
  2. customto afford the crude
  3. customThe residue obtained
  4. extractionextracted with ethylacetate
  5. washwashed with saturated NaHCO3 solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-121c2f297c9b4638992670ef5f71ce78
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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