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 872446Notes

Reaction equation

HRID 872446 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1104c7fbe90c4097aa04deb938dc398c
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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