Hydrochloric Acid → N,N-dimethyl-1-[6-(1-naphthylsulfonyl)-2,3-dihydro[1,4]oxazino[2,3,4-hi]indazol-2-yl]methanamine Hydrochloride

HRID 33111Notes

Reaction equation

[Cl:1][CH2:2][CH:3]1[CH2:13][N:12]2[C:14]3[C:9]([C:10]([S:15]([C:18]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])=[N:11]2)=[CH:8][CH:7]=[CH:6][C:5]=3[O:4]1.[CH3:28][NH:29][CH3:30].Cl.CCOCC>CS(C)=O.O>[ClH:1].[CH3:28][N:29]([CH3:30])[CH2:2][CH:3]1[O:4][C:5]2=[C:14]3[C:9](=[CH:8][CH:7]=[CH:6]2)[C:10]([S:15]([C:18]2[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[N:11][N:12]3[CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-chloromethyl-2-(naphthalene-1-sulfonyl)-7,8-dihydro-6-oxa-1,8a-diaza-acenaphthylene (0.075 g, 0.18 mmoles) and dimethylamine (0.56 ml, 1M solution in THF, 0.56 mmoles) in DMSO was stirred under nitrogen at 100° C. for 4 hours, cooled to room temperature, diluted with water and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by flash chromatography using as eluent 5% CH3OH/EtOAc. The purified compound was dissolved in methanol, treated with 1M HCl in ether (0.2 ml, 0.2 mmoles) and evaporated to dryness to afford the title compound, MS: (ES) m/z 407.

Workup

temperaturecooled to room temperature
extractionextracted with EtOAc
washwashed sequentially with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customThe resultant residue was purified by flash chromatography
dissolutionThe purified compound was dissolved in methanol
customevaporated to dryness

Sources & evidence

ORD record: ord-54107132d07d48338dc750a18208c17c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429582B2

Reaction notes

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