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

HRID 229096노트

반응식

HRID 229096 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
85 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-cc2d5cb395af49998c0631ffefbec38e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560586B2

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