Triethylamine → HCID 123236452, compound

HRID 1477680Notes

Reaction equation

HRID 1477680 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:4](=[O:16])[N:3]=1.C(N(CC)CC)C.[CH3:24][C:25]1([CH3:38])[C:29]([CH3:31])([CH3:30])[O:28][B:27]([C:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH:37]=2)[O:26]1>C(Cl)(Cl)Cl.O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:5]2[CH:6]=[N:7][C:2]([N:35]3[CH2:34][CH2:33][C:32]([B:27]4[O:28][C:29]([CH3:31])([CH3:30])[C:25]([CH3:38])([CH3:24])[O:26]4)=[CH:37][CH2:36]3)=[N:3][C:4]2=[O:16])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 211054611,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 117839620HCID 117839620, compound

Product 1

HCID 123236452HCID 123236452, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a chloroform solution (3.0 mL) of 4-chloro-1-(4-chlorobenzyl)-1,3,5-triazin-2(1H)-one (128 mg, 0.500 mmol) synthesized in Reference Synthesis Example 11, triethylamine (70.0 μL, 0.500 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (156 mg, 0.750 mmol) were added and the resultant mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with chloroform was performed. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→4/1) to obtain the title compound (86.0 mg, yield 40%).

Workup

  1. additionwere added
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→4/1)

Sources & evidence

ORD record
ord-b79a9bf4b730424e83799c832c62e776
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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