Diisopropylethylamine → Methyl 4-(4-(4-(allyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

HRID 2042709Notes

Reaction equation

HRID 2042709 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)[N:3]=1.[CH2:25]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH2:36])=[CH:31][CH:30]=1)[CH:26]=[CH2:27].CCN(C(C)C)C(C)C>C1COCC1>[CH2:25]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH:36][C:2]2[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[N:5]=[C:4]([NH:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)[N:3]=2)=[CH:31][CH:30]=1)[CH:26]=[CH2:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 218436204-(2-Propen-1-yloxy)benzenemethanamineHCID 86652469Methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

Product 1

HCID 67074750Methyl 4-(4-(4-(allyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoateYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (500 mg, 1.38 mmol) in THF (5 mL) was added (4-(allyloxy)phenyl)methanamine (275 mg, 1.38 mmol) and iPr2NEt (0.96 mL, 5.51 mmol). The mixture was stirred at room temperature for 16 hours. The solvent was removed under vacuum. The residue was purified via silica gel column (EtOAC/Hexanes=4:1) to give methyl 4-(4-(4-(allyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (0.2 g, 30%) as a white solid.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was purified via silica gel column (EtOAC/Hexanes=4:1)

Sources & evidence

ORD record
ord-b74c6185746f4bafb10a5328bfe1785d
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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