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

HRID 1993692Notes

Reaction equation

HRID 1993692 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[N:25]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)[N:26]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:28]=3)=[O:22])=[C:16]([CH3:40])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:41]>CO>[ClH:41].[ClH:41].[C:29]([C:27]1[CH:28]=[C:24]([NH:23][C:21]([NH:20][C:17]2[C:16]([CH3:40])=[N:15][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:19][CH:18]=2)=[O:22])[N:25]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)[N:26]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 685368704-{5-[3-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-6-methyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a 22° C. solution of 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-6-methyl-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (Preparation 49; 63.20 g, 115.4 mmol) in MeOH (600 mL) with HCl (4 N solution in dioxane, 300 mL, 1200 mmol). Stir the mixture for 4 hours then concentrate under reduced pressure (room temperature, ca. 10 torr, 3 days) to afford 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(2-methyl-6-piperazin-1-yl-pyridin-3-yl)-urea dihydrochloride as an off-white powder (62.2 g—contains ca. 45 mol % of dioxane. LCMS(ES+): m/z=448 [M+H].

Workup

  1. concentrationthen concentrate under reduced pressure (room temperature, ca. 10 torr, 3 days)

Sources & evidence

ORD record
ord-cade32e4c40d48f2b0037e0507429f1e
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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