Hydrochloric Acid → HCID 58972439, compound

HRID 2264501Notes

Reaction equation

HRID 2264501 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]([NH:21][CH2:22][CH2:23][OH:24])[N:18]=[C:17]([O:25][CH3:26])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:26][O:25][C:17]1[N:16]=[C:15]([NH:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[N:20]=[C:19]([NH:21][CH2:22][CH2:23][OH:24])[N:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 68781601HCID 68781601, compound

Product 1

HCID 58972439HCID 58972439, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-[4-(2-hydroxy-ethylamino)-6-methoxy-[1,3,5]triazin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 2.7 mmol, 1.0 equiv) in ethanol (30 mL) was added 4 M HCl in dioxane (3.40 mL, 13.6 mmol, 5.0 equiv) drop by drop. The reaction mixture was subsequently stirred at rt for 72 h and at 80° C. for 2 h. It was then cooled down to rt, poured into ice water and the pH was adjusted to 9-10 by addition of a sat. solution of potassium carbonate. The solution was extracted six times with a mixture of dichloromethane/isopropanol (4:1). The combined organic layers were concentrated by evaporation under reduced pressure to yield 0.60 g (83%) of the title compound as light yellow oil. MS (ISP): 269.2 [M+H]+.

Workup

  1. temperatureIt was then cooled down to rt
  2. extractionThe solution was extracted six times
  3. additionwith a mixture of dichloromethane/isopropanol (4:1)
  4. concentrationThe combined organic layers were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5a8db8634f0545bd80bf84eacda0b24b
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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