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 2064169노트

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HRID 2064169 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-80ce39c1345c44eb8a8778bdf277fddf
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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