Sodium Bicarbonate → 8-(2-Chloro-6-fluoro-3,5-dimethoxyphenyl)-N-(5-((4-ethylpiperazin-1-yl)methyl)pyridin-2-yl)quinoxaline-5-carboxamide

HRID 43180Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]2[N:8]=[CH:9][CH:10]=[N:11][C:12]=2[C:13]([C:16]2[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=2[Cl:27])=[CH:14][CH:15]=1)=O)C.[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([NH2:43])=[N:41][CH:42]=2)[CH2:32][CH2:31]1)[CH3:29].C[Al](C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO.C(Cl)Cl>[CH2:28]([N:30]1[CH2:31][CH2:32][N:33]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([NH:43][C:4]([C:6]3[C:7]4[N:8]=[CH:9][CH:10]=[N:11][C:12]=4[C:13]([C:16]4[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=4[Cl:27])=[CH:14][CH:15]=3)=[O:3])=[N:41][CH:42]=2)[CH2:34][CH2:35]1)[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

The title compound was prepared in analogy to the procedure described in Example 115 but using 8-(2-chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 144.1), 5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-ylamine (Example 26.1; purified by silica gel column chromatography), 2 equiv of trimethyl aluminum, stirring the reaction mixture for 7 h at 80° C., pouring it onto a saturated aqueous solution of NaHCO3 and DCM. Title compound: ESI-MS: 564.8 [M+H]+; tR=3.57 min (System 1); TLC: Rf=0.25 (DCM/MeOH/NH3aq, 94:5:1).

Workup

customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record: ord-37e636e89f39436da97abafda814a760
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536175B2

Reaction notes

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