Sulfuric acid magnesium salt (1:1) → (2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

HRID 1827515노트

반응식

HRID 1827515 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N:17]1([CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:7]=[CH:6][C:3]=1[CH2:4][NH:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:26][CH:27]=1

참가 물질

7

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)anilineHCID 221373212-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde

생성물 1

HCID 22137435(2-Chloro-4-(tetrahydro-pyran-2-yloxy)-benzyl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine수율 71.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-chloro-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (1.68 g, 6.97 mmol) and 4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (1.37 g, 6.64 mmol) in 25 mL methylene chloride was added magnesium sulfate (2.81 g, 23.3 mmol). The reaction mixture was stirred under nitrogen at room temperature overnight, then was filtered, and concentrated. The residue was dissolved in 25 mL of 2:1 (v/v) ethanol:methanol and was treated with sodium borohydride (1.51 g, 39.84 mmol) in portions added over 1 hr. The reaction mixture was stirred at room temperature for 2 hr. at which time it was concentrated to one-half of its original volume. To this mixture was added 25 mL water and 25 mL saturated aqueous sodium bicarbonate. The mixture was extracted with methylene chloride and the organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography of the residue (methylene chloride to 10% methanol/methylene chloride) afforded 2.04 g (71%) of the title compound. MS 431.1 (M+1)+

후처리

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 25 mL of 2:1 (v/v) ethanol
  4. additionadded over 1 hr
  5. stirringThe reaction mixture was stirred at room temperature for 2 hr
  6. concentrationat which time it was concentrated to one-half of its original volume
  7. additionTo this mixture was added 25 mL water and 25 mL saturated aqueous sodium bicarbonate
  8. extractionThe mixture was extracted with methylene chloride
  9. dry with materialthe organic layer was dried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c64c777568bc45e1961798c263bc79b1
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053212B2

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