Hydrochloric Acid → 4-(3-methyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one

HRID 2234067Notes

Reaction equation

C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[C:9]1[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:21]=[N:20][C:19]=1[O:30]C)=O)(C)(C)C.Cl>C(O)C.[OH-].[Na+]>[CH3:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:9]=1[C:18]1[C:19](=[O:30])[NH:20][N:21]=[C:22]([C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)[CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

50 mg 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-methyl-indole-1-carboxylic acid tert-butyl ester is dissolved in 0.75 ml ethanol and 0.75 ml 1N aqueous NaOH solution. The reaction mixture is stirred at 150° C. in microwave apparatus (200 W). The solution is neutralized by addition of 1N HCl, the solvent removed under reduced pressure and the crude product purified by HPLC chromatography (RP18 column, acetonitril/water, 0.05% HCOOH) yielding 21.1 mg 4-(3-methyl-1H-indol-2-yl)-6-pyridin-4-yl-2H-pyridazin-3-one.

Workup

customthe solvent removed under reduced pressure
customthe crude product purified by HPLC chromatography (RP18 column, acetonitril/water, 0.05% HCOOH)

Sources & evidence

ORD record: ord-2b5ad5e7435748a7966f679e3e3caa9c
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709466B2

Reaction notes

Loading…