1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea dihydrochloride → 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea

HRID 1993693Notes

Reaction equation

HRID 1993693 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:8]=[C:9]([NH:19][C:20]([NH:22][C:23]2[C:24]([CH3:35])=[N:25][C:26]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:27][CH:28]=2)=[O:21])[N:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:11]=1)([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([C:7]1[CH:8]=[C:9]([NH:19][C:20]([NH:22][C:23]2[C:24]([CH3:35])=[N:25][C:26]([N:29]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]3)=[CH:27][CH:28]=2)=[O:21])[N:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:11]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

3

Reactant 1

HCID 685368091-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea dihydrochloride

Product 1

HCID 685352231-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-ureaYield 72.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Load a solution of 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea dihydrochloride (10 g, 19.2 mmol) in MeOH onto a 70 g Varian SCX column, rinsing with MeOH (ca. 300 mL). Elute the free base with 1:1 2 M ammonia in MeOH:dichloromethane (150 mL). Concentrate under reduced pressure to give a white solid (6.24 g). LCMS(ES+): m/z=448 [M+H].

Workup

  1. washElute the free base with 1:1 2 M ammonia in MeOH
  2. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-892686c98f064aa6b2dacc69c81b7ad4
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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