三乙胺 → N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide

HRID 38249

反应方程式

HRID 38249 反应方程式
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH2:27][CH2:26]2)=[C:21]([Cl:36])[CH:20]=1>C(Cl)Cl>[Cl:36][C:21]1[CH:20]=[C:19]([NH:18][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:24]=[CH:23][C:22]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH2:27][CH2:26]1

参与物

5

反应物 3

HCID 8471三乙胺HCID 135033吡啶-2-甲酰氯盐酸盐HCID 9369261-[4-(4-氨基-2-氯-苯基)-哌嗪-1-基]-2-甲基-丙-1-酮

产物 1

HCID 42645025N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide收率 18%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

According to Scheme 4 Step 3: Picolinoyl chloride hydrochloride (0.93 mmol, 178 mg) and Et3N (1.86 mmol, 0.26 mL) were added to a solution of 1-(4-(4-amino-2-chlorophenyl)piperazin-1-yl)-2-methylpropan-1-one (0.62 mmol, 175 mg) in DCM (3 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over C18 column using water/ACN (60:40) as eluent to afford N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide (0.11 mmol, 42 mg, 18%) as a white solid.

后处理

  1. washThe organic phase was washed with a saturated solution of NaHCO3
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over Na2SO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography over C18 column

来源与证据

ORD记录
ord-bf9a8f47cc0d45d592b8c2e6d4a9879b
来源数据集
uspto-grants-2013_09
专利号
US08524726B2

关联笔记

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