1-Methylpiperazine → HCID 178481042, compound

HRID 872440Notes

Reaction equation

HRID 872440 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[O:20][C:19]([CH2:21][CH2:22][NH:23][C:24]([C:26]3[NH:30][N:29]=[C:28]([C:31](O)=[O:32])[CH:27]=3)=[O:25])=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]>>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[O:20][C:19]([CH2:21][CH2:22][NH:23][C:24]([C:26]3[NH:30][N:29]=[C:28]([C:31]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[O:32])[CH:27]=3)=[O:25])=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 1785244995-{2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylcarbamoyl}-1H-pyrazole-3-carboxylic acid

Product 1

HCID 178481042HCID 178481042, compoundYield 35%

Procedure

The title compound was synthesized as in Example 1 starting from 1-methylpiperazine and 5-{2-[5-(3,4-dichlorophenyl)furan-2-yl]ethylcarbamoyl}-1H-pyrazole-3-carboxylic acid. Crude product was purified by chromatography (CombiFlash, silica column, eluent 0-10% MeOH/DCM) and crystallized from DCM/heptane to give 1.06 g (35%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.19 (s, 3H), 2.33 (br s, 4H), 2.95 (t, 2H), 3.56 (q, 2H), 3.62 (br s, 2H), 3.85 (br s, 2H), 6.34 (d, 1H), 7.02 (d, 1H), 7.07 (br s, 1H), 7.60 (dd, 1H), 7.63 (d, 1H), 7.84 (d, 1H), 8.61 (s, 1H), 13.92 (s, 1H).

Workup

  1. customCrude product was purified by chromatography (CombiFlash, silica column, eluent 0-10% MeOH/DCM)
  2. customcrystallized from DCM/heptane

Sources & evidence

ORD record
ord-b0596d312be149499724837ce009066e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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