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

HRID 41539

Reaction equation

Cl.[C:2]1(=[O:13])[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].Cl[C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1>CN(C=O)C>[N:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:29]=[CH:30][C:21]=1[N:10]1[CH2:11][CH2:12][C:7]2([C:2](=[O:13])[NH:3][CH2:4][CH2:5][CH2:6]2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 60 °C

Procedure

To the stirred solution of 2,9-diazaspiro[5.5]undecan-1-one hydrochloride (2.2 g, 10.78 mmol) in DMF (15 mL) was added K2CO3 (4.45 g, 32.24 mmol) and 2-chloro quinoxaline (1.94 g, 11.82 mmol). The mixture was heated at 60° C. for 18 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the crude mixture water was added and extracted with ethyl acetate. The organic layer was dried over anhydride sodium sulfate, filtered and concentrated to obtain a yellow solid which was triturated with n-pentane to yield a yellow solid (2.5 g, 78%). [1H-NMR (DMSO-d6, 300 MHz): δ 8.91 (s, 1H), 7.81 (d, 1H), 7.62-7.55 (m, 2H), 7.42-7.33 (m, 2H), 4.33-4.19 (m, 2H), 3.52-3.33 (m, 2H), 3.20-3.05 (m, 2H), 2.12-1.98 (m, 2H), 1.95-1.64 (m, 4H), 1.59-1.48 (m, 2H); HPLC RtA=3.665 min (97%); LCMS RtA=0.377, [M+H]+=297.1].

Workup

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated under reduced pressure
additionTo the crude mixture water was added
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydride sodium sulfate
filtrationfiltered
concentrationconcentrated
customto obtain a yellow solid which
customwas triturated with n-pentane

Sources & evidence

ORD record: ord-36b22e4738d444ec836995891d8da21a
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530648B2

Linked notes

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