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

HRID 872445Notes

Reaction equation

HRID 872445 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.Cl.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[O:22][C:21]([CH2:23][CH2:24][NH2:25])=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]>>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[O:22][C:21]([CH2:23][CH2:24][NH:25][C:6]([C:4]3[N:3]=[CH:2][NH:1][CH:5]=3)=[O:8])=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

3

Reactant 2

HCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochlorideHCID 178524800HCID 178524800, compound

Product 1

HCID 1785231341H-Imidazole-4-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide

Procedure

The title compound was prepared as in Example 12 starting from 4-imidazolecarboxylic acid and 2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylamine hydrochloride. The crude product was purified by flash chromatography using CH2Cl2/MeOH as a gradient eluent (100:0-99.6:0.4). The product was triturated in ethyl acetate. 1H NMR (400 MHz, DMSO-d6): 2.93 (21-1, t), 3.55 (2H, m), 6.33 (1H, d), 7.01 (1H, d), 7.59 (1H, s), 7.63 (2H, s), 7.71 (1H, s), 7.87 (1H, s), 8.05 (1H, broad s), 12.43 (1H, broad s).

Workup

  1. customThe crude product was purified by flash chromatography
  2. customThe product was triturated in ethyl acetate

Sources & evidence

ORD record
ord-fc435af890c54a0fba2e8f9a6f323676
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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