Ammonium Chloride → HCID 117760218, compound

HRID 709834Notes

Reaction equation

HRID 709834 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][C:26]2([C:31]#[N:32])[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:13]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[F:24])=[N:14][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1>[F:24][C:17]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=1[C:13]1[C:12]([CH2:25][C:26]2([C:31]#[N:32])[CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 131733923HCID 131733923, compound

Product 1

HCID 117760218HCID 117760218, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-((5-(((tert-butyl(dimethyl)silyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methyl)cyclopentanecarbonitrile (514 mg) in THF (10 mL) was added a THF solution (1 M, 2.2 mL) of tetrabutylammonium fluoride, and the mixture was stirred at room temperature for 20 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (355 mg) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-416f7b03430f4b2e9ed684910672413f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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