Potassium Carbonate → 9-(Quinoxalin-2-yl)-1,9-diazaspiro[5.5]undecan-2-one

HRID 41559Notes

Reaction equation

[NH:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:12].Cl[C:14]1[CH:23]=[N:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:22]=[CH:23][C:14]=1[N:9]1[CH2:10][CH2:11][C:6]2([NH:1][C:2](=[O:12])[CH2:3][CH2:4][CH2:5]2)[CH2:7][CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 1,9-diazaspiro[5.5]undecan-2-one (TFA salt) (800 mg, 4.76 mmol) in 10 mL DMF, 2-chloroquinoxaline (937 mg, 5.71 mmol) and K2CO3 (3.3 g, 23.8 mmol) were added and the reaction mixture was stirred for 18 h at 80° C. under a nitrogen atmosphere. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (2×50 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by flash column chromatography (eluent: 3% methanol in chloroform) to yield the title compound (1.0 g, 71%). [LCMS RtF=0.37 min, [M+H]+=297.2]

Workup

customThe reaction mixture was quenched with ice-cold water
extractionextracted with ethyl acetate (2×50 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude mixture was purified by flash column chromatography (eluent: 3% methanol in chloroform)

Sources & evidence

ORD record: ord-951ffd16e84c468fb584470bfaab2dbc
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530648B2

Reaction notes

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