HCID 86637295, compound → HCID 86637294, compound

HRID 1876875Notes

Reaction equation

HRID 1876875 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([CH2:27][C:28]#[N:29])([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[N:21]=3)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.F[Si-2](F)(F)(F)(F)F.[H+].[H+]>C(#N)C>[Cl:26][C:22]1[N:21]=[C:20]([C:18]2[CH:17]=[N:16][N:15]([C:12]3([CH2:27][C:28]#[N:29])[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH2:11]3)[CH:19]=2)[CH:25]=[CH:24][N:23]=1

Participants

3

Reactant 1

HCID 86637295HCID 86637295, compound

Product 1

HCID 86637294HCID 86637294, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-(tert-butyl(dimethyl)silyl)oxy-1-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)cyclohexylacetonitrile (1.8 g, 0.0042 mol) in acetonitrile (69.74 mL) was added fluorosilicic acid (2.0 M in water, 4.17 mL). The mixture was stirred at room temperature overnight. After evaporation of most of the solvent, the mixture was neutralized with aqueous sodium bicarbonate, extracted with ether. The organic layers were combined, washed with brine, dried over MgSO4, and concentrated to dryness. The residue (a 1:3.5 mixture of cis- and trans-isomers) was used directly in next step (1.20 g, 90.6%). LCMS (M+H) 318.3.

Workup

  1. customAfter evaporation of most of the solvent
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. additionThe residue (a 1:3.5 mixture of cis- and trans-isomers)

Sources & evidence

ORD record
ord-6021cf75ae0c4c93b8df30ceaba08bd1
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

Loading…