2,4-Dichloro-1,3,5-triazine → HCID 118023188, compound

HRID 522637Notes

Reaction equation

HRID 522637 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][C@@H:27]([OH:31])[CH2:26]2)=[CH:21][CH:20]=1>O1CCOCC1>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][CH2:28][C@@H:27]([OH:31])[CH2:26]3)=[CH:21][CH:20]=2)[N:7]=1

Participants

5

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 28803426HCID 28803426, compound

Product 1

HCID 118023188HCID 118023188, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2,4-dichloro-1,3,5-triazine in dioxane was added diisopropylethylamine, followed by the addition of (R)-1-(4-aminophenyl)piperidin-3-ol. The reaction mixture was stirred at 110° C. for 1 hour, and LCMS (liquid chromatography-mass spectrometry) showed the reaction was completed. The solvents were removed under reduced pressure, and the residue was purified by silica gel chromatography, eluting with petroleum ether:ethyl acetate=5:1, to afford (R)-1-(4-((4-chloro-1,3,5-triazin-2-yl)amino)phenyl)piperidin-3-ol.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with petroleum ether

Sources & evidence

ORD record
ord-066c066be85d407582fe7e1cc27d3e19
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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