Tetrafluoroboric acid → HCID 69743175, compound

HRID 1760046Notes

Reaction equation

HRID 1760046 reaction equation
F[B-](F)(F)F.[H+].N([O-])=O.[Na+].O1CCOCC1.N[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C@@H:25]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:26]([N:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][C:32]([O:40][CH3:41])=[C:33]([O:38][CH3:39])[CH:34]=2)[CH2:29]1)=[O:27]>[Cu-]=O.O>[C:19]1([NH:24][C@@H:25]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:26]([N:28]2[CH2:37][CH2:36][C:35]3[C:30](=[CH:31][C:32]([O:40][CH3:41])=[C:33]([O:38][CH3:39])[CH:34]=3)[CH2:29]2)=[O:27])[CH:20]=[CH:21][CH:22]=[CH:23][CH:18]=1

Participants

7

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 312751,4-Dioxane2×HCID 20748464HCID 20748464, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 69743175HCID 69743175, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolvent

Procedure

Tetrafluoroboric acid (1.5 ml) and an aqueous sodium nitrite solution (20 mg/0.2 ml, 0.29 mmol) were added, at 0° C., to a dioxane (2 ml) solution of (2S)-2-[(2aminophenyl)amino]-1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3,3dimethylbutan-1-one (100 mg, 0.25 mmol) obtained in Example 25, and the mixture was stirred at that temperature for 30 minutes. Copper (I) oxide (75 mg, 0.52 mmol) was added to the reaction solution, and the mixture was stirred for 30 minutes. Dioxane (2 ml) and water (10 ml) were added to the mixture, and the mixture was concentrated under reduced pressure. The residue was extracted twice with chloroform (each 5 ml), and the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography using hexane and ethyl acetate (2:1) as an eluent to obtain the captioned compound (68.0 mg, 70%) as a green oily substance.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionThe residue was extracted twice with chloroform (each 5 ml), and the extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-4445743d773743b89cf88c177901d8de
Source dataset
uspto-grants-2005_01
Patent number
US06838465B2

Reaction notes

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