Potassium Carbonate → tert-Butyl (2-{[2-(5-cyanopyridin-2-yl)ethyl]amino}ethyl)carbamate

HRID 1466049Notes

Reaction equation

HRID 1466049 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][N:9]=1)(=O)=O.[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH2:25])([CH3:19])([CH3:18])[CH3:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][NH:25][CH2:24][CH2:23][NH:22][C:21](=[O:26])[O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[N:9][CH:10]=1)#[N:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 187201N-BOC-ethylenediamineHCID 895250142-(5-Cyanopyridin-2-yl)ethyl methanesulfonate

Product 1

HCID 121005078tert-Butyl (2-{[2-(5-cyanopyridin-2-yl)ethyl]amino}ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(5-cyanopyridin-2-yl)ethyl methanesulfonate (4.0 g, crude), tert-butyl(2-aminoethyl)carbamate (4.8 g, 30 mmol) and K2CO3 (3.2 g, 30 mmol) in 40 mL of DMF was stirred overnight at room temperature. The reaction mixture was poured into ice water and extracted with EtOAc (100 mL×3). The combined EtOAc layer was washed with brine and concentrated. The residue was purified by silica gel column (DCM:MeOH=10:1) to afford the title compound.

Workup

  1. extractionextracted with EtOAc (100 mL×3)
  2. washThe combined EtOAc layer was washed with brine
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-3ac84b3389784ee9b6bafda99b9851ff
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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