Hydrochloric Acid → (2-{[1-(3-chlorobenzyl)-5-fluoro-3-(1-naphthylsulfonyl)-1H-indazol-7-yl]oxy}ethyl)methylamine Hydrochloride

HRID 2240062Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:19])=[CH:12][C:13]=2[O:15][CH2:16][CH2:17]Cl)[C:8]([S:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[N:7]1.[CH3:36][NH2:37].Cl.CCOCC>CS(C)=O.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([F:19])=[CH:12][C:13]=2[O:15][CH2:16][CH2:17][NH:37][CH3:36])[C:8]([S:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)(=[O:21])=[O:22])=[N:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(3-chloro-benzyl)-7-(2-chloro-ethoxy)-5-fluoro-3-(naphthalene-1-sulfonyl)-1H-indazole (0.075 g, 0.14 mmoles) and methylamine (0.56 mmoles) in DMSO (1 mL) was stirred under nitrogen at 100° C. for 4 hours. Mixture was cooled to room temperature, diluted with water, extracted with EtOAc, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. Compound was purified by flash chromatography using as eluent 5% CH3OH/EtOAc. The purified compound was dissolved in methanol, 1M HCl in ether (0.1 mL, 0.1 mmoles) was added, and compound was dried to afford the title compound as the HCl salt.

Workup

temperatureMixture was cooled to room temperature
extractionextracted with EtOAc
washwashed with water (2×), brine (1×)
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customCompound was purified by flash chromatography
dissolutionThe purified compound was dissolved in methanol
customcompound was dried

Sources & evidence

ORD record: ord-47a234e406b94272976c6369552f52ca
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723329B2

Reaction notes

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