4-Fluorobenzyl chloride → [1-(4-Fluoro-benzyl)-piperidin-4-yl]-methyl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

HRID 1426380노트

반응식

HRID 1426380 반응식
[CH3:1][N:2]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:3]1[S:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][N:7]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>C(#N)C.ClCCl>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:15]2[CH2:16][CH2:17][CH:12]([N:2]([CH3:1])[C:3]3[S:4][C:5]([C:8]([F:11])([F:9])[F:10])=[N:6][N:7]=3)[CH2:13][CH2:14]2)=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 96024-Fluorobenzyl chlorideHCID 81531DiisopropylethylamineHCID 59323568Methyl-piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine

생성물 1

HCID 25022336[1-(4-Fluoro-benzyl)-piperidin-4-yl]-methyl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine수율 87%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
120 °C

실험 절차

A mixture of methyl-piperidin-4-yl-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-amine (D2) (0.050 g, 0.19 mmol), 4-fluorobenzyl chloride (0.029 ml, 0.24 mmol) and diisopropylethylamine (0.050 ml, 0.28 mmol) in acetonitrile (3 ml) was stirred at 120° C. for 30 min., under microwave irradiation. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and extracted with a 10% solution of ammonium chloride (25 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 0-1.5% ammonia in methanol (7M)/dichloromethane) to yield E1 (0.061 g, 87%) as a solid. C16H18F4N4S requires 374. Found 375 (MH+).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with a 10% solution of ammonium chloride (25 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica gel; 0-1.5% ammonia in methanol (7M)/dichloromethane)

출처 및 근거

ORD 기록
ord-d3a3a0e8410249f29b9dcab13905795c
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933101B2

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