Hydrochloric Acid → 8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (1H-imidazol-2-yl)-amide

HRID 1189744Notes

Reaction equation

C[Si](C)(C)CCOC[N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[NH:12][C:13]([C:15]1[C:16]2[N:17]=[CH:18][CH:19]=[N:20][C:21]=2[C:22]([C:25]2[C:30]([Cl:31])=[C:29]([O:32][CH3:33])[CH:28]=[C:27]([O:34][CH3:35])[C:26]=2[Cl:36])=[CH:23][CH:24]=1)=[O:14].Cl.C([O-])([O-])=O.[Na+].[Na+]>CCO>[NH:9]1[CH:10]=[CH:11][N:7]=[C:8]1[NH:12][C:13]([C:15]1[C:16]2[N:17]=[CH:18][CH:19]=[N:20][C:21]=2[C:22]([C:25]2[C:26]([Cl:36])=[C:27]([O:34][CH3:35])[CH:28]=[C:29]([O:32][CH3:33])[C:30]=2[Cl:31])=[CH:23][CH:24]=1)=[O:14]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid [1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-amide (Step 14.1) (0.527 g, 0.82 mmol), 5 N HCl (7 mL), and EtOH (4 mL) was stirred at 65° C. for 10 h. The reaction mixture was allowed to cool to rt, basified by addition of a saturated aqueous solution of Na2CO3, and extracted with DCM. The combined organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 0.288 g of the title compound as a yellow solid: ESI-MS: 443.9/445.9 [M+H]+; tR=3.74 min (System 1); TLC: Rf=0.30 (DCM/MeOH/NH3aq, 94:5:1).

Workup

temperatureto cool to rt
extractionextracted with DCM
washThe combined organic phase was washed with H2O and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record: ord-85f098983885470da73aaa2113fb280d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674099B2

Reaction notes

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