Dipropylamine → Ethyl {[2-(cyclohexylamino)-3-pyridyl]imino}(diethylamino)methylcarbamate

HRID 11286

Reaction equation

HRID 11286 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:15]([O:17][C:18]([N:20]=[C:21]=S)=[O:19])[CH3:16].[CH2:23]([NH:26][CH2:27][CH2:28]C)[CH2:24]C>CN(C=O)C>[CH:9]1([NH:8][C:3]2[C:2]([N:1]=[C:21]([NH:20][C:18](=[O:19])[O:17][CH2:15][CH3:16])[N:26]([CH2:27][CH3:28])[CH2:23][CH3:24])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 85320Ethyl isothiocyanatoformateHCID 109870832-N-cyclohexylpyridine-2,3-diamine

Product 1

HCID 136335149Ethyl {[2-(cyclohexylamino)-3-pyridyl]imino}(diethylamino)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 0.02 mol (3.82 g) of 3-amino-2-cyclohexylaminopyridine from Preparation 1 and 0.02 mol of ethoxycarbonyl isothiocyanate is stirred in 50 ml of DMF at ambient temperature for 3 hours. The solution is then cooled to 0° C., and 0.05 mol of dipropylamine and then 0.02 mol of mercuric chloride are added in succession. After 15 minutes, the ice bath is removed and the solution is stirred at ambient temperature for 4 hours. After diluting the solution with 100 ml of ethyl acetate, filtration is carried out over Celite and the solvents are evaporated off under reduced pressure. The resulting crude product is then recrystallised from acetonitrile.

Workup

  1. customthe ice bath is removed
  2. additionAfter diluting the solution
  3. filtrationwith 100 ml of ethyl acetate, filtration
  4. customthe solvents are evaporated off under reduced pressure
  5. customThe resulting crude product is then recrystallised from acetonitrile

Sources & evidence

ORD record
ord-b54805a8be0d4495a08ee3d78f19e951
Source dataset
uspto-grants-2006_08
Patent number
US07098220B2

Linked notes

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