Hydrochloric Acid → HCID 58972453, compound

HRID 2264509Notes

Reaction equation

HRID 2264509 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]([O:21][S:22]([CH3:25])(=[O:23])=[O:24])=[CH:19][N:20]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 86615300HCID 86615300, compound

Product 1

HCID 58972453HCID 58972453, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(5-methanesulfonyloxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.85 g, 2.3 mmol, 1.0 equiv) in ethanol (15 mL) was added 4 M HCl in dioxane (2.85 mL, 11.4 mmol, 5.0 equiv) and the mixture was warmed up to 50° C. After 16 h, the reaction mixture was cooled down to rt, then poured into ice water and the pH was adjusted to 9-10 by addition of a sat. solution of potassium carbonate. Then, this solution was extracted three times with dichloromethane/isopropanol (4:1). The combined organic layers were concentrated by evaporation under reduced pressure to yield 0.62 g (99%) of the title compound as a colorless solid. MS (ISP): 273.0 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled down to rt
  2. extractionThen, this solution was extracted three times with dichloromethane/isopropanol (4:1)
  3. concentrationThe combined organic layers were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e27033d5ac6f46bda6d98c47ef0e3393
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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