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 872446노트

반응식

HRID 872446 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1104c7fbe90c4097aa04deb938dc398c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975254B2

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