Acetone Cyanohydrin → HCID 59683269, compound

HRID 447780Notes

Reaction equation

HRID 447780 reaction equation
Cl.[F:2][C:3]1[C:11]2[NH:10][C:9](=[O:12])[N:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:7]=2[CH:6]=[C:5]([CH3:19])[C:4]=1[F:20].[O:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.CC(C)(O)[C:30]#[N:31].S([O-])([O-])(=O)=O.[Mg+2]>CC(N(C)C)=O>[F:2][C:3]1[C:11]2[NH:10][C:9](=[O:12])[N:8]([CH:13]3[CH2:14][CH2:15][N:16]([C:24]4([C:30]#[N:31])[CH2:25][CH2:26][O:21][CH2:22][CH2:23]4)[CH2:17][CH2:18]3)[C:7]=2[CH:6]=[C:5]([CH3:19])[C:4]=1[F:20]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 24083Sulfuric acid magnesium salt (1:1)HCID 121599Tetrahydro-4H-pyran-4-oneHCID 68624356HCID 68624356, compound

Product 1

HCID 59683269HCID 59683269, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

4,5-Difluoro-6-methyl-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D23, 90 mg, 0.3 mmol) was converted to its free base using SCX, and this was then mixed with tetrahydro-4H-pyran-4-one (100 mg, 1.2 mmol), acetone cyanohydrin (100 mg, 1.2 mmol), magnesium sulfate (0.33 g) and dimethylacetamide (1 ml). The mixture was stirred under a slow stream of argon at 60° C. overnight, then partitioned between water and dichloromethane. Drying and evaporation gave the crystalline title compound from diethyl ether, 70 mg.

Workup

  1. custompartitioned between water and dichloromethane
  2. customDrying
  3. customevaporation

Sources & evidence

ORD record
ord-f3feeddb89d941ad8d1dc41370014519
Source dataset
uspto-grants-2013_07
Patent number
US08481566B2

Reaction notes

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