Acetic Acid → HCID 58972434, compound

HRID 2264413Notes

Reaction equation

HRID 2264413 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(=O)C>Br.O>[CH2:21]([C:18]1[CH:19]=[N:20][C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:16][CH:17]=1)[CH3:22]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 68784762HCID 68784762, compound

Product 1

HCID 58972434HCID 58972434, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 4-(5-ethyl-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (4.53 g, 16.3 mmol) in 48% HBr in water (45 mL) and acetic acid (45 mL) was heated to 100° C. After 4 h the solvents were removed under reduced pressure and the crude reaction product extracted from a solution of 1 M NaOH (200 mL) with ethyl acetate (3×100 mL). The combined organic phases were dried over MgSO4 and concentrated by evaporation under reduced pressure to yield 3.1 g (92%) of the title compound which was directly used in the consecutive step. MS (ISP): 207.1 [M+H]+.

Workup

  1. customAfter 4 h the solvents were removed under reduced pressure
  2. customthe crude reaction product
  3. extractionextracted from a solution of 1 M NaOH (200 mL) with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b53a25e6bf254fcfabe7c742e793f848
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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