Ammonium fluoride → HCID 86619572, compound

HRID 1929890Notes

Reaction equation

HRID 1929890 reaction equation
[CH:1]1([C@:4]([OH:32])([CH3:31])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12]([C:15]#[C:16][Si](CC)(CC)CC)=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1.[F-].[NH4+]>CO>[CH:1]1([C@:4]([OH:32])([CH3:31])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12]([C:15]#[CH:16])=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 68877372HCID 68877372, compound

Product 1

HCID 86619572HCID 86619572, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.40 g 6-(4-chloro-phenyl)-5-triethylsilanylethynyl-pyrazine-2-carboxylic acid ((R)-2-cyclopropyl-2-hydroxy-propyl)-amide in 10 ml methanol was added at room temperature 0.40 g ammonium fluoride and the mixture was stirred at room temperature for 30 min. The orange reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 6-(4-chloro-phenyl)-5-ethynyl-pyrazine-2-carboxylic acid ((R)-2-cyclopropyl-2-hydroxy-propyl)-amide as light yellow foam.

Workup

  1. customThe orange reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-e67366f38bbc4eb3957b4353997c37b7
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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