1,4-Dioxane hydrochloride → 5-(2,4-Dihydroxy-5-isopropylphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-2,4-dihydro-[1,2,4]triazol-3-one

HRID 1947212Notes

Reaction equation

Cl.O1CCOCC1.[CH:8]([C:11]1[C:12]([O:41]COC)=[CH:13][C:14]([O:37]COC)=[C:15]([C:17]2[N:18]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)=[CH:25][CH:24]=3)[C:19](=[O:22])[NH:20][N:21]=2)[CH:16]=1)([CH3:10])[CH3:9]>CO>[OH:37][C:14]1[CH:13]=[C:12]([OH:41])[C:11]([CH:8]([CH3:10])[CH3:9])=[CH:16][C:15]=1[C:17]1[N:18]([C:23]2[CH:24]=[CH:25][C:26]([CH2:29][N:30]3[CH2:31][CH2:32][N:33]([CH3:36])[CH2:34][CH2:35]3)=[CH:27][CH:28]=2)[C:19](=[O:22])[NH:20][N:21]=1

Participants

Conditions

Temperature: 40 °C

Procedure

At room temperature, 4 N hydrochloric acid/1,4-dioxane solution (5 mL) was added to a methanol (5 mL) solution of 5-(5-isopropyl-2,4-bis-methoxymethoxyphenyl)-4-[4-(4-methyl piperazin-1-ylmethyl)phenyl]-2,4-dihydro-[1,2,4]triazol-3-one (F652-09, 644 mg, 1.26 mmol). After stirring at 40° C. for 1 hour, the solvent was distilled off under reduced pressure. Methanol was added to the crude product thus obtained, and the resulting suspension was stirred at room temperature. The precipitated solid was collected by filtration to obtain 5-(2,4-dihydroxy-5-isopropylphenyl)-4-[4-(4-methylpiperazin-1-ylmethyl)phenyl]-2,4-dihydro-[1,2,4]triazol-3-one (OH-a13) dihydrochloride (white solids).

Workup

distillationthe solvent was distilled off under reduced pressure
additionMethanol was added to the crude product
customthus obtained
stirringthe resulting suspension was stirred at room temperature
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-f8309d77c0494fc7b46e66720e4179dc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399464B2

Reaction notes

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