Acetone Cyanohydrin → HCID 59683269, compound

HRID 2061492Notes

Reaction equation

HRID 2061492 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-73fc53f885d541c3aa4cfc1471b3c676
Source dataset
uspto-grants-2012_10
Patent number
US08283364B2

Reaction notes

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