Potassium Fluoride → HCID 67246418, compound

HRID 2425431Notes

Reaction equation

HRID 2425431 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].[K+].C[Si]([C:34]([F:37])([F:36])[F:35])(C)C>CN(C)C=O.[Cu]Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([C:34]([F:37])([F:36])[F:35])=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 67242852(S)-3-(tert-Butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

Product 1

HCID 67246418HCID 67246418, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of Intermediate 1a (200 mg) prepared in Example 1-1, Step A in N,N-dimethylformamide (5 ml) was added with potassium fluoride (30.8 mg, Aldrich), trimethylsilyltrifluoromethane (0.196 ml, Aldrich), and copper(I) chloride (65.2 mg, Wako Pure Chemical Industries), and the mixture was stirred at 60° C. for 15 hours. The reaction mixture was cooled to room temperature, and then the insoluble solids were removed by filtration through Celite. The solvent was evaporated under reduced pressure, and the residue was separated and purified by HPLC to obtain the title compound (16.3 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble solids were removed by filtration through Celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was separated
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-1987b02e0ae5445fac64aa8dc1cb173a
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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