1,3-Dibromopropane → Tert-butyl 4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate

HRID 1485659Notes

Reaction equation

HRID 1485659 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[OH:36])[CH2:5][NH:6][C:7]1[N:12]=[C:11]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:10]=[C:9]([NH:19][C:20]2[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][CH:21]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].[Br:43][CH2:44][CH2:45][CH2:46]Br>CC(C)=O>[Br:43][CH2:44][CH2:45][CH2:46][O:36][C:35]1[CH:34]=[CH:33][C:4]([CH2:5][NH:6][C:7]2[N:12]=[C:11]([O:13][CH2:14][C:15]([F:17])([F:16])[F:18])[N:10]=[C:9]([NH:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[CH:22][CH:21]=3)[N:8]=2)=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 90101730Tert-butyl 4-((4-((3-chloro-4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate

Product 1

HCID 90102380Tert-butyl 4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a dry 30 mL vial equipped with a stir bar was added tert-butyl 4-((4-((3-chloro-4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate (1.80 g, 3.18 mmol), potassium carbonate (1.32 g, 9.55 mmol) and acetone (16 mL). To the mixture was added 1,3-dibromopropane (3.37 ml, 25.5 mmol). The vial was placed in a 60° C. heating block with stirring for 2.5 h. The mixture was cooled to room temperature and then concentrated in vacuo. The resulting solid residue was subjected to SiO2 chromatography (hexanes:EtOAc 85:15 to 75:25) to afford tert-butyl 4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate as a colorless solid (1.60 g, 78%). MS m/z=646.25 (M+H)+.

Workup

  1. customTo a dry 30 mL vial equipped with a stir bar
  2. customwas placed in a 60° C.
  3. temperatureheating block
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dffa7025dcd440bb97dbdc397300da1f
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

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