Potassium Carbonate → 9-(quinoxalin-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one

HRID 41552

Reaktionsgleichung

[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][N:21]3[C:26]4([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH2:25][CH2:24][CH2:23][C:22]3=[O:32])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl[C:34]1[CH:43]=[N:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:42]=[CH:43][C:34]=1[N:29]1[CH2:30][CH2:31][C:26]2([N:21]([CH2:20][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[CH:13]=[CH:12][N:11]4[S:1]([C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=3)(=[O:2])=[O:3])[C:22](=[O:32])[CH2:23][CH2:24][CH2:25]2)[CH2:27][CH2:28]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one (TFA salt) (0.11 g, 0.201 mmol) in 5.0 mL DMF, 2-chloroquinoxaline (0.04 g, 0.241 mmol) and K2CO3 (0.084 g, 0.603 mmol) were added and the reaction mixture was stirred for 6 h at 80° C. under a nitrogen atmosphere. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (2×25 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to yield the title compound as a pale yellow solid (0.120 g). LCMS RtA=0.512, [M+H]+=579.9

Aufarbeitung

customThe reaction mixture was quenched with ice-cold water
extractionextracted with ethyl acetate (2×25 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-ddff8d2dee554227b8146a6e133499cb
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08530648B2

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