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

HRID 41539

반응식

HRID 41539 반응식
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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2389382-ChloroquinoxalineHCID 450742882,9-Diazaspiro(5.5)undecan-1-one hydrochloride

생성물 1

HCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 78.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-36b22e4738d444ec836995891d8da21a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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