三乙胺 → 9-Chloro-3-methyl-5-[1-(3-pyridin-2-yl-propionyl)-piperidin-3-yl]-5H-isoxazolo[4,3-c]quinolin-4-one

HRID 2212195

反应方程式

HRID 2212195 反应方程式
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][C:32](O)=[O:33].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([C:32](=[O:33])[CH2:31][CH2:30][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=4)[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

参与物

8

反应物 5

HCID 8471三乙胺HCID 181649N-羟基-7-氮杂苯并三氮唑HCID 5642923-吡啶-2-基-丙酸HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

产物 1

HCID 219637209-Chloro-3-methyl-5-[1-(3-pyridin-2-yl-propionyl)-piperidin-3-yl]-5H-isoxazolo[4,3-c]quinolin-4-one收率 77.6%

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

Add 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol), 2-pyridine propionic acid (20 mg, 0.13 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 0.13 mmol), 1-hydroxy-7-azabenzotriazole (18 mg, 0.13 mmol), 4-dimethylamino-pyridine (1 mg, 0.01 mmol), and dimethylformamide (3 mL) to a dry roundbottom flask. Stir the reaction under nitrogen, and add triethylamine (30 μL, 0.22 mmol) dropwise. Stir the solution under nitrogen at room temperature overnight. Concentrate the solution and dissolve in 20% isopropanol/chloroform; wash with saturated aqueous sodium bicarbonate solution and brine; dry over magnesium sulfate; and concentrate. Purify by flash chromatography on silica gel (eluting with 0–2% methanol/chloroform) to give 38.5 mg of the title compound as a white solid, 76% yield. 1H NMR: consistent with structure. MS (ion spray) 451 (M+).

后处理

  1. customthe reaction under nitrogen
  2. stirringStir the solution under nitrogen at room temperature overnight
  3. concentrationConcentrate the solution
  4. dissolutiondissolve in 20% isopropanol/chloroform
  5. washwash with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdry over magnesium sulfate
  7. concentrationand concentrate
  8. customPurify by flash chromatography on silica gel (eluting with 0–2% methanol/chloroform)

来源与证据

ORD记录
ord-1d0529684373416cb15e36ac09d2a65f
来源数据集
uspto-grants-2006_09
专利号
US07101891B2

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