Triethylamine → 1-(4-Chlorobenzyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazin-2(1H)-one

HRID 1477680노트

반응식

HRID 1477680 반응식
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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 211054611,2,3,6-Tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 1178396204-chloro-1-(4-chlorobenzyl)-1,3,5-triazin-2(1H)-one

생성물 1

HCID 1232364521-(4-Chlorobenzyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl]-1,3,5-triazin-2(1H)-one수율 40.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-b79a9bf4b730424e83799c832c62e776
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403798B2

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