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

HRID 1426380ノート

反応式

HRID 1426380 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
120 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-d3a3a0e8410249f29b9dcab13905795c
出典データセット
uspto-grants-2015_01
特許番号
US08933101B2

反応ノート

読み込み中…