Potassium Carbonate → HCID 86625871、化合物

HRID 1485579

反応式

HRID 1485579 の反応式
[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

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 7238334-(N-Boc-amino)piperidineHCID 131266993-Bromopyridazine

生成物 1

HCID 86625871HCID 86625871、化合物収率 35.4%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-23525637b4f04fb6a18f2c15dd65498f
出典データセット
uspto-grants-2016_08
特許番号
US09422298B2

関連ノート

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