Hydrochloric Acid → HCID 178484419, compound

HRID 2240081Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([S:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[N:10][NH:11]2)=[CH:7][CH:6]=1.[CH3:27][NH2:28].Cl.CCOCC>CS(C)=O.O>[ClH:1].[CH3:27][NH:28][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([S:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[N:10][NH:11]2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-(2-chloro-ethoxy)-3-(naphthalene-1-sulfonyl)-1-H-indazole (0.075 g, 0.19 mmoles) and methylamine (0.28 mL, 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 (0.2 mL, 0.2 mmoles) was added, then dried, to afford the title compound as the HCl salt (0.07 g, 0.19 mmoles), MS: (ES+) 381 [M+H]+

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
customdried

Sources & evidence

ORD record: ord-a84eeca576204905822eaee112301b3f
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723329B2

Reaction notes

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