Sodium Iodide → 3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-propoxy}-4-methyl-benzoic acid hydrochloride salt

HRID 229096ノート

反応式

HRID 229096 の反応式
Br[CH2:2][CH2:3][CH2:4][OH:5].[Na+].[I-].[C:8]([O-:11])([O-])=[O:9].[K+].[K+].[C:14]1([CH:20]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:21][NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:25]=2[Cl:34])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[ClH:34].[Cl:34][C:25]1[C:26]([C:30]([F:31])([F:32])[F:33])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:22]([CH2:21][CH:20]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:2][CH2:3][CH2:4][O:5][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:14]=1[CH3:20])[C:8]([OH:11])=[O:9]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 58913799(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amine

生成物 1

HCID 688622453-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]-propoxy}-4-methyl-benzoic acid hydrochloride salt収率 65%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

To a stirring solution of 3-bromo-propanol (77 ul, 0.84 mmol) in acetonitrile (10 ml) was added NaI (0.25 g, 1.7 mmol) and K2CO3 (0.23 g, 1.7 mmol). The mixture was stirred at 85° C. for 1 h, and then N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethyl-benzyl)amine (0.43 g, 1.12 mmol) was added. The reaction mixture was heated at 85° C. overnight. Solvent was removed, the residue was washed with H2O, and extracted twice with EtOAc. The EtOAc extracts were dried over Na2SO4, filtered, and concentrated. The crude mixture was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to give 225 mg (60%) of the title compound as a white solid. MS (ESI) 448.0 (M+H+).

後処理

  1. temperatureThe reaction mixture was heated at 85° C. overnight
  2. customSolvent was removed
  3. washthe residue was washed with H2O
  4. extractionextracted twice with EtOAc
  5. dry with materialThe EtOAc extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude mixture was purified by preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm)

出典と根拠

ORDレコード
ord-cc2d5cb395af49998c0631ffefbec38e
出典データセット
uspto-grants-2009_07
特許番号
US07560586B2

反応ノート

読み込み中…