5-(2-Furyl)-1-phenyl-1H-pyrazole-3-carboxylic acid → 5-Furan-2-yl-1-phenyl-1H-pyrazole-3-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide

HRID 872443Notes

Reaction equation

HRID 872443 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([C:17]([OH:19])=O)[CH:7]=1.Cl.[Cl:21][C:22]1[CH:23]=[C:24]([C:29]2[O:33][C:32]([CH2:34][CH2:35][NH2:36])=[CH:31][CH:30]=2)[CH:25]=[CH:26][C:27]=1[Cl:28]>>[Cl:21][C:22]1[CH:23]=[C:24]([C:29]2[O:33][C:32]([CH2:34][CH2:35][NH:36][C:17]([C:8]3[CH:7]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[N:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:9]=3)=[O:19])=[CH:31][CH:30]=2)[CH:25]=[CH:26][C:27]=1[Cl:28]

Participants

3

Reactant 2

HCID 27716215-(2-Furyl)-1-phenyl-1H-pyrazole-3-carboxylic acidHCID 671683442-(5-(3,4-Dichlorophenyl)furan-2-yl)ethanamine hydrochloride

Product 1

HCID 671714255-Furan-2-yl-1-phenyl-1H-pyrazole-3-carboxylic acid {2-[5-(3,4-dichlorophenyl)furan-2-yl]ethyl}amide

Procedure

The title compound was prepared as in Example 12 starting from 5-(2-furyl)-1-phenyl-1H-pyrazole-3-carboxylic acid and 2-[5-(3,4-dichlorophenyl)furan-2-yl]-ethylamine hydrochloride. The crude product was purified twice by flash chromatography using first CH2Cl2-MeOH as a gradient eluent (100:0-99:1). Then another purification by flash chromatography was done by using heptane/EtOAc (8:2) as an eluent. 1H NMR (400 MHz, DMSO-d6): 2.96 (2H, t), 3.58 (2H, m), 6.16 (1H, d), 6.34 (1H, d), 6.51 (1H, dd), 7.01 (1H, d), 7.07 (1H, s), 7.45-7.48 (2H, m), 7.54-7.56 (4H, m), 7.61 (1H, distorted dd), 7.73 (1H, d), 7.84 (1H, d), 8.49 (1H, t, 3J=5.9 Hz).

Workup

  1. customThe crude product was purified twice by flash chromatography
  2. customThen another purification by flash chromatography

Sources & evidence

ORD record
ord-c56585abe1604e0ab644c68abf7a76f3
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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