Dimethylformamide → N-(5-(5-(azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 405858ノート

反応式

HRID 405858 の反応式
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[N:24]1([C:28]2[O:32][N:31]=[C:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([N+:40]([O-])=O)[CH:34]=3)[N:29]=2)[CH2:27][CH2:26][CH2:25]1>ClCCl.N1C=CC=CC=1>[N:24]1([C:28]2[O:32][N:31]=[C:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([NH:40][C:10]([C:3]4[N:4]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]5=[N:1][CH:2]=4)=[O:12])[CH:34]=3)[N:29]=2)[CH2:27][CH2:26][CH2:25]1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 712815105-(Azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

生成物 1

HCID 71281134N-(5-(5-(azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirring suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (71 mg, 0.39 mmol) in anhydrous dichloromethane (2 mL) was added dropwise oxalyl chloride (173 uL, 1.98 mmol). Then, a drop of anhydrous N,N-dimethylformamide was added and the reaction mixture was stirred at room temperature for 30 minutes. The solvent was concentrated. A stirring mixture of the acid chloride and 5-(azetidin-1-yl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (109) (85 mg, 0.29 mmol) in anhydrous pyridine (2 mL) was stirred at room temperature for 30 minutes. The crude product was purified on silica gel using 10% MeOH in dichloromethane to give N-(5-(5-(azetidin-1-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F77). 1H NMR (400 MHz, CD2Cl2) δ 10.10 (s, 1H), 9.51-9.48 (m, 1H), 8.65 (s, 1H), 7.94 (d, J=1.6 Hz, 1H), 7.86-7.83 (m, 1H), 7.71 (dd, J=1.6, 7.6 Hz, 1H), 7.64-7.60 (m, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.27-7.24 (m, 1H), 4.26-4.22 (m, 4H), 2.48-2.40 (m, 2H), 2.34 (s, 3H). MS m/z 374.15 (M+1)+.

後処理

  1. concentrationThe solvent was concentrated
  2. stirringwas stirred at room temperature for 30 minutes
  3. customThe crude product was purified on silica gel using 10% MeOH in dichloromethane

出典と根拠

ORDレコード
ord-f43c706b7de34434881dfc2149a709d7
出典データセット
uspto-grants-2014_06
特許番号
US08754071B2

反応ノート

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