反応 #308556

ord-ba0fd363aa7f4327a8d40be6875a7a71

反応方程式

CCOC(=O)c1nc(-c2ccncc2)no1
3-pyridin-4-yl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester
CCCCCC1CCC(N)CC1
4-pentylcyclohexylamine
C[CH2][Al]([CH2]C)[CH2]C
triethylaluminium
O=C([O-])O.[Na+]
NaHCO3
CCCCCC1CCC(NC(=O)c2nc(-c3ccncc3)no2)CC1
title compound
CCCCCC1CCC(NC(=O)c2nc(-c3ccncc3)no2)CC1
3-Pyridin-4-yl-[1,2,4]oxadiazole-5-carboxylic acid (4-pentylcyclohexyl)amide

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The organic phase was separated
  2. 2
    洗浄washed with brine (5 ml)
  3. 3
    乾燥dried (MgSO4)
  4. 4
    その他The solvent was evaporated
  5. 5
    その他the residue purified by flash chromatography

実験手順

A solution of 3-pyridin-4-yl-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (50.5 mg, 0.23 mmol) and 4-pentylcyclohexylamine (39 mg, 0.23 mmol) in anhydrous toluene (2 ml) was treated with triethylaluminium (345 μl of a 2M solution in hexanes, 0.69 mmol). After stirring at rt for 18 h, saturated aqueous NaHCO3 (2 ml) was added and the mixture diluted with CH2Cl2 (25 ml). The organic phase was separated, washed with brine (5 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography to afford the title compound: RT=4.14 min; m/z (ES+)=343.2 [M+]+.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08207147B2uspto-grants-2012_06