Water → tert-Butyl (2-((5-cyanopyridin-2-yl)amino)ethyl)carbamate

HRID 2171482Notes

Reaction equation

HRID 2171482 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=1.C(=O)(O)[O-].[K+].O>CN(C=O)C>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([NH:11][CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[N:14][CH:15]=1)#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 187201N-BOC-ethylenediamineHCID 516893Potassium BicarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 47453716tert-Butyl (2-((5-cyanopyridin-2-yl)amino)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3.0 g (18.73 mmol) of N-Boc-ethylenediamine, 5.19 g (37.45 mmol) of 6-chloronicotinonitrile and 3.75 g (37.45 mmol) of potassium bicarbonate are suspended in 360 ml of DMF and heated at 90° C. for 16 h. Water is added to the mixture, which is then extracted three times with ethyl acetate. The combined organic phases are washed with saturated aqueous sodium chloride solution. After drying over magnesium sulphate, the solvent is removed. Drying under high vacuum results in 3.58 g (68% of theory) of the product.

Workup

  1. extractionis then extracted three times with ethyl acetate
  2. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  3. dry with materialAfter drying over magnesium sulphate
  4. customthe solvent is removed
  5. customDrying under high vacuum
  6. customresults in 3.58 g (68% of theory) of the product

Sources & evidence

ORD record
ord-2993fde398824422b4646520aab4b8e6
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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