Potassium Carbonate → HCID 90102385, compound

HRID 1485650Notes

Reaction equation

HRID 1485650 reaction equation
[OH:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:11]=[C:10]([NH:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][CH:3]=1.[Cl:36][CH2:37][C:38]([CH2:40]Cl)=[CH2:39].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:36][CH2:37][C:38](=[CH2:39])[CH2:40][O:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:17])[F:18])[N:11]=[C:10]([NH:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158593-Chloro-2-chloromethyl-1-propeneHCID 58223050Tert-butyl 4-((4-((4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate

Product 1

HCID 90102385HCID 90102385, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of tert-butyl 4-((4-((4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate (3 g), 3-chloro-2-(chloromethyl)prop-1-ene (1.15 g) and K2CO3 (1.69 g) in acetone (20 mL) was heated to reflux for 16 hours. The solvent was removed under vacuum. The residue was purified by silica gel column (hexanes:EtOAc=10:1 to 4:1) to give tert-butyl 4-(4-(4-(2-(chloromethyl)allyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (1.3 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed under vacuum
  4. customThe residue was purified by silica gel column (hexanes:EtOAc=10:1 to 4:1)

Sources & evidence

ORD record
ord-62f835c2ac074a1bbc659df54c35b329
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

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