Ammonium fluoride → HCID 86619572, compound

HRID 1159286Notes

Reaction equation

HRID 1159286 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 aceate, 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 aceate
  2. customthe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-b5988e72f8194417979cdbb127a83504
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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