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

HRID 2389743Notes

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

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

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

Sources & evidence

ORD record: ord-48c70eb719fe4515b715382c8781d94d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273752B2

Reaction notes

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