Dimethylformamide → 4'-{[2-Cyclopropyl-4-(4-fluorobenzyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 1412146노트

반응식

HRID 1412146 반응식
[CH:1]1([C:4]2[N:31]=[C:7]3[NH:8][C:9](=[O:30])[C:10]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([C:22]5[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=5)=[CH:18][CH:17]=4)=[C:11]([CH2:12][CH2:13][CH3:14])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.Br[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH:1]1([C:4]2[N:31]=[C:7]3[N:8]([CH2:33][C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[C:9](=[O:30])[C:10]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([C:22]5[C:23]([C:28]#[N:29])=[CH:24][CH:25]=[CH:26][CH:27]=5)=[CH:18][CH:17]=4)=[C:11]([CH2:12][CH2:13][CH3:14])[N:6]3[N:5]=2)[CH2:2][CH2:3]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 1363371384'-[(2-Cyclopropyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile

생성물 1

HCID 670099144'-{[2-Cyclopropyl-4-(4-fluorobenzyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile수율 70%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4′-[(2-cyclopropyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (0.5 g), 1-(bromomethyl)-4-fluorobenzene (0.17 mL), potassium carbonate (0.34 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogensulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.44 g, 70%).

후처리

  1. washwashed with 5% aqueous potassium hydrogensulfate solution
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-61c241e2ea52409ea86ae3d2dd738fce
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921379B2

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