Acetone Cyanohydrin → 4-{4-[6-Chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrile

HRID 2064169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064169
Cl.[F:2][C:3]([F:22])([F:21])[C:4]1[C:19]([Cl:20])=[CH:18][C:7]2[N:8]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=1.[CH3:23][C:24]([CH3:28])(O)[C:25]#[N:26].[O:29]1[CH2:34]CC(=O)C[CH2:30]1.CC(N(C)C)=O>C(OCC)(=O)C.O>[Cl:20][C:19]1[C:4]([C:3]([F:21])([F:2])[F:22])=[CH:5][C:6]2[NH:10][C:9](=[O:11])[N:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:24]4([C:25]#[N:26])[CH2:28][CH2:34][O:29][CH2:30][CH2:23]4)[CH2:14][CH2:13]3)[C:7]=2[CH:18]=1

Komponenten

7

Edukt 4

HCID 6406Acetone CyanohydrinHCID 31374DimethylacetamideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 691287645-Trifluoromethyl-6-chloro-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride

Produkt 1

HCID 598501594-{4-[6-Chloro-2-oxo-5-(trifluoromethyl)-2,3-dihydro-1H-benzimidazol-1-yl]-1-piperidinyl}tetrahydro-2H-pyran-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Trifluoromethyl-6-chloro-1-(4-piperidinyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (D64, 850 mg) was converted to the free base using SCX then combined with acetone cyanohydrin (400 mg), tetrahydropyran-4-one (500 mg) magnesium sulphate (1.5 g) and dimethylacetamide (2.5 ml), and the mixture heated under a slow stream of argon for 18 h at 60° C. To the cooled mixture were added water and ethyl acetate. The organic layer was dried over MgSO4, filtered and evaporated, and the residue was crystallised from diethyl ether to afford the subtitle compound, 160 mg.

Aufarbeitung

  1. dry with materialThe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. customevaporated
  4. customthe residue was crystallised from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-80ce39c1345c44eb8a8778bdf277fddf
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288412B2

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