碳酸钾 → HCID 86625871，化合物

HRID 1485579

反应方程式

HRID 1485579 反应方程式
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[C:16]1[N:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[F-].[Cs+].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl.O>[N:17]1[CH:16]=[CH:21][CH:20]=[C:19]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[N:18]=1

参与物

8

反应物 4

HCID 11430碳酸钾HCID 25953氟化铯HCID 7238334-叔丁氧羰基氨基哌啶HCID 131266993-溴哒嗪

产物 1

HCID 86625871HCID 86625871，化合物收率 35.4%

试剂、催化剂与溶剂 3

HCID 679二甲基亚砜溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6344二氯甲烷溶剂

反应条件

温度
100 °C

实验过程

The reaction mixture of tert-butyl piperidin-4-ylcarbamate (250 mg, 1.25 mmol), 3-bromopyridazine (258 mg, 1.62 mmol), CsF (37.9 mg, 0.25 mmol), and K2CO3 (518 mg, 3.74 mmol) in DMSO (12.5 mL) was heated at 100° C. for 20 h. Water and DCM were poured into the mixture, and the separated aqueous layer was extracted with DCM, the combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo. The residue was purified by column chromatography (Hexane:EtOAc=1:1) to give tert-butyl 1-(pyridazine-3-yl)piperidin-4-ylcarbamate (123 mg, 35%) as a pale yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.45 (9H, s), 1.92-2.12 (2H, m), 3.03-3.17 (2H, m), 3.55-3.80 (2H, m), 4.25-4.38 (2H, m), 4.52 (1H, brs), 6.92 (1H, d, J=9.2 Hz), 7.20 (1H, dd, J=4.4, 9.2 Hz), 8.56 (1H, d, J=4.4 Hz). NH peak was not observed. m/z=279.06 [M+1]+.

后处理

  1. extractionthe separated aqueous layer was extracted with DCM
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (Hexane:EtOAc=1:1)

来源与证据

ORD记录
ord-23525637b4f04fb6a18f2c15dd65498f
来源数据集
uspto-grants-2016_08
专利号
US09422298B2

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