2-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride → HCID 178427027, compound

HRID 872455Notes

Reaction equation

HRID 872455 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[NH:4][N:3]=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]>>[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[NH:4][N:3]=[C:2]([CH3:1])[CH:6]=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 178427254HCID 178427254, compound

Product 1

HCID 178427027HCID 178427027, compoundYield 28%

Procedure

The title compound was prepared using the method of Example 20 starting from 3-methyl-1H-pyrazole-5-carboxylic acid and 2-(5-(3,4-dichlorophenyl)furan-2-yl)ethanamine hydrochloride. Crude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane) to obtain 301 mg (28%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.25 (s, 3H), 2.92 (t, 2H), 3.53 (q, 2H), 6.32 (d, 1H), 6.34 (s, 1H), 7.01 (d, 1H), 7.63 (m, 2H), 7.85 (s, 1H), 8.16 (t, 1H), 13.86 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customCrude product was purified by chromatography (CombiFlash, silica column, eluent: 0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-97bc3adb0ddf4a3689ea2dbd7d034dea
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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