Citric Acid → HCID 66990791, 화합물

HRID 454507노트

반응식

HRID 454507 반응식
[C:1]1(OB=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16]([O:23][C:24]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:38][C:25]=1[C:26]([NH:28][C:29]1[CH:34]=[C:33](Cl)[CH:32]=[CH:31][C:30]=1[C:36]#[N:37])=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)(Cl)Cl.COCCOC.O>[CH2:16]([O:23][C:24]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:38][C:25]=1[C:26]([NH:28][C:29]1[CH:34]=[C:33]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:32]=[CH:31][C:30]=1[C:36]#[N:37])=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

8

반응물 4

HCID 311Citric AcidHCID 10340Sodium Carbonate2회HCID 14438906HCID 14438906, 화합물2회HCID 669898292-(benzyloxy)-N-(5-chloro-2-cyanophenyl)-5-(piperidin-1-yl)benzamide

생성물 1

HCID 66990791HCID 66990791, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 80711,2-Dimethoxyethane용매

실험 절차

Water (0.74 mL), phenylboranic acid (0.12 g), sodium carbonate (0.21 g), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) dichloride (3.0 mg) were added to an ethylene glycol dimethyl ether (3.0 mL) suspension of the obtained 2-(benzyloxy)-N-(5-chloro-2-cyanophenyl)-5-(piperidin-1-yl)benzamide, followed by heating to reflux under a nitrogen atmosphere for 1 hour. After cooling the reaction mixture to room temperature, phenylboranic acid (0.12 g), sodium carbonate (0.21 g), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) dichloride (3.0 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 40 minutes. The reaction mixture was cooled to room temperature, and then chloroform and a 10% aqueous solution of citric acid were added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 90-50% hexane/ethyl acetate] to obtain 0.32 g of 2-(benzyloxy)-N-(4-cyanobiphenyl-3-yl)-5-(piperidin-1-yl)benzamide as a yellow solid.

후처리

  1. temperatureby heating
  2. temperatureto reflux under a nitrogen atmosphere for 1 hour
  3. temperatureby heating
  4. temperatureto reflux under a nitrogen atmosphere for 40 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [eluent: 90-50% hexane/ethyl acetate]

출처 및 근거

ORD 기록
ord-6728fa4c038744cfb83e74bf78c67344
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492582B2

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