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

HRID 444809Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[C:10]([NH:17][CH2:18][CH2:19][NH2:20])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.C(OCC)(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:20][CH2:19][CH2:18][NH:17][C:10](=[O:11])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[N:3][CH:4]=1)#[N:7]

Participants

Conditions

Temperature: 90 °C

Procedure

5.5 g (39.7 mmol) of 6-chloronicotinonitrile were dissolved in 70 ml of DMSO, and 10.2 g (63.5 mmol) of N-Boc-ethylenediamine and 11 g (79.4 mmol) of potassium carbonate were added. The mixture was stirred at 90° C. for 12 h. The residue was taken up in a mixture of water and ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. The residue was chromatographed on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 10:1 to 2:1). This gave 7.9 g (77% of theory) of the product as a solid.

Workup

washThe organic phase was washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated on a rotary evaporator
customThe residue was chromatographed on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 10:1 to 2:1)

Sources & evidence

ORD record: ord-bec0db614ec244dcb3fcf5937457dc21
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476267B2

Reaction notes

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