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Dimethylformamide → N3-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3,6-dicarboxamide

HRID 1497927
ノート
印刷プレビュー

反応式

HRID 1497927 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([OH:15])=O)=[CH:11][N:12]=2)[CH:9]=1)(=[O:3])[NH2:2].C(Cl)(=O)C(Cl)=O.CN(C)C=O.C[NH:28][C:29]1[CH:34]=[C:33]([C:35]2[N:39]=[C:38]([CH:40]3[CH2:43][C:42]([F:45])([F:44])[CH2:41]3)[O:37][N:36]=2)[CH:32]=[CH:31][C:30]=1[CH3:46]>ClCCl.N1C=CC=CC=1>[F:45][C:42]1([F:44])[CH2:41][CH:40]([C:38]2[O:37][N:36]=[C:35]([C:33]3[CH:32]=[CH:31][C:30]([CH3:46])=[C:29]([NH:28][C:13]([C:10]4[N:8]5[CH:9]=[C:4]([C:1]([NH2:2])=[O:3])[CH:5]=[CH:6][C:7]5=[N:12][CH:11]=4)=[O:15])[CH:34]=3)[N:39]=2)[CH2:43]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 679761586-Carbamoylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 71280889Methyl 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline

生成物 1

HCID 71280471N3-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3,6-dicarboxamide

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirring suspension of 6-carbamoylimidazo[1,2-a]pyridine-3-carboxylic acid (110) (50 mg, 0.172 mmol) in anhydrous dichloromethane (2 mL) at 0° C. under Argon was added dropwise oxalyl chloride (16 uL, 0.189 mmol). Then, a drop of anhydrous N,N-dimethylformamide was added and the reaction mixture was stirred at 0° C. for 1 hour. The solvent was concentrated. A stirring mixture of the acid chloride and methyl 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) (23 mg, 0.0861 mmol) in anhydrous pyridine (2 mL) was stirred at room temperature for 20 minutes. The crude product was purified by reverse phase preparative HPLC to give N3-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3,6-dicarboxamide (F62). 1H NMR (400 MHz, d6-DMSO) δ 10.18 (s, 1H), 9.99-9.98 (m, 1H), 8.68 (s, 1H), 8.28 (s, 1H), 8.10 (d, J=1.6 Hz, 1H), 7.98 (dd, J=1.6, 9.2 Hz, 1H), 7.88-7.83 (m, 2H), 7.66 (s, 1H), 7.52 (d, J=8.0 Hz, 1H), 3.91-3.84 (m, 1H), 3.22-3.06 (m, 4H), 2.38 (s, 3H). MS m/z 452.14 (M+1)+.

後処理

  1. concentrationThe solvent was concentrated
  2. stirringwas stirred at room temperature for 20 minutes
  3. customThe crude product was purified by reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-e0d96b0a59604984a6a447fa1e3f73dc
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09199981B2

反応ノート

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