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 2064169ノート

反応式

HRID 2064169 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-80ce39c1345c44eb8a8778bdf277fddf
出典データセット
uspto-grants-2012_10
特許番号
US08288412B2

反応ノート

読み込み中…