Methanol → HCID 71251930, compound

HRID 2411977Notes

Reaction equation

CO.[OH-].[Na+].C([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[N:14]=[N:15][C:16]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[C:32]([CH3:33])=[CH:31][C:30]([CH:34]5[CH2:36][CH2:35]5)=[CH:29][N:28]=4)[CH2:23][CH2:22]3)=[O:20])=[CH:17][CH:18]=2)[C:9]1=[O:37])(=O)C>O>[CH:34]1([C:30]2[CH:31]=[C:32]([CH3:33])[C:27]([N:24]3[CH2:25][CH2:26][N:21]([C:19]([C:16]4[N:15]=[N:14][C:13]([N:10]5[CH2:11][CH2:12][NH:8][C:9]5=[O:37])=[CH:18][CH:17]=4)=[O:20])[CH2:22][CH2:23]3)=[N:28][CH:29]=2)[CH2:35][CH2:36]1

Participants

Conditions

Temperature: 40 °C

Procedure

Using (6-chloropyridazin-3-yl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (179 mg) described in Preparation Example 233 and 1-acetylimidazolidin-2-one (64 mg) and by the reaction and treatment in the same manner as in Example 511, 1-acetyl-3-{6-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]pyridazin-3-yl}imidazolidin-2-one was obtained as a crude product (170 mg). Methanol (1.2 mL) and 1N aqueous sodium hydroxide solution (0.57 mL) were added to the obtained crude product (170 mg) of 1-acetyl-3-{6-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]pyridazin-3-yl}imidazolidin-2-one, and the mixture was stirred at 40° C. for 1 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The solvent was evaporated, and the residue was purified by column chromatography (ethyl acetate:methanol) to give the title compound (48 mg).

Workup

temperatureAfter cooling
extractionthe mixture was extracted with ethyl acetate
customThe solvent was evaporated
customthe residue was purified by column chromatography (ethyl acetate:methanol)

Sources & evidence

ORD record: ord-884462fa123d4118a18f06dc5d218e57
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816079B2

Reaction notes

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