2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride → 2-Methyl-1H-imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide hydrochloride

HRID 872446ノート

反応式

HRID 872446 の反応式
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.Cl.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2[O:23][C:22]([CH2:24][CH2:25][NH2:26])=[CH:21][CH:20]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]>>[ClH:11].[Cl:11][C:12]1[CH:13]=[C:14]([C:19]2[O:23][C:22]([CH2:24][CH2:25][NH:26][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=3)=[O:9])=[CH:21][CH:20]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]

参加物

3

反応物 2

HCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochlorideHCID 178433052HCID 178433052、化合物

生成物 1

HCID 1784330422-Methyl-1H-imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide hydrochloride

実験手順

The title compound was prepared as in Example 12 starting from 2-methyl-1H-imidazole-4-carboxylic acid and 2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylamine hydrochloride. The crude product was purified by flash chromatography using CH—2Cl2/MeOH as a gradient eluent (100:0-97:3). The product was dissolved in DCM, ethyl acetate saturated with hydrogen chloride was added and the precipitated product as a hydrogen chloride salt was filtered. Recrystallization from MeOH/EtOAc. The HCl salt: 1H NMR (400 MHz, MeOH-d4): 2.62 (3H, s), 3.02 (1H, t), 3.69 (1H, t), 6.26 (1H, d), 6.76 (1H, d), 7.49 (1H, distorted d), 6.53 (1H, distorted dd), 7.71 (1H, d), 7.82 (1H, s).

後処理

  1. customThe crude product was purified by flash chromatography
  2. dissolutionThe product was dissolved in DCM
  3. additionethyl acetate saturated with hydrogen chloride was added
  4. filtrationthe precipitated product as a hydrogen chloride salt was filtered
  5. customRecrystallization from MeOH/EtOAc

出典と根拠

ORDレコード
ord-1104c7fbe90c4097aa04deb938dc398c
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

反応ノート

読み込み中…