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

HRID 41554

반응식

HRID 41554 반응식
OC(C(F)(F)F)=O.[C:8]1(=[O:19])[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][NH:9]1.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.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.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:16]1[CH2:17][CH2:18][C:13]2([C:8](=[O:19])[NH:9][CH2:10][CH2:11][CH2:12]2)[CH2:14][CH2:15]1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 2389382-ChloroquinoxalineHCID 468615352,9-Diazaspiro[5.5]undecan-1-one trifluoroacetate

생성물 1

HCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 78.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매

반응 조건

온도
160 °C

실험 절차

The mixture of 2,9-diazaspiro[5.5]undecan-1-one TFA salt ([1190586-22-1], 1.0 g, 3.5 mmol), 2-chloroquinoxaline ([1448-87-9], 0.77 g, 4.6 mmol), DIPEA (3.7 ml, 21 mmol) and DMAP (22 mg, 0.18 mmol) in ethanol (10 ml) was placed in a microwave tube. The tube was sealed and the suspension was heated at 160° C. for 2 h under microwave conditions. The mixture was filtered and the residue washed with ethanol. The filtrate was concentrated and the precipitate filtered and washed with ethanol. The combined solid material was dissolved in ethyl acetate, washed with water and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 0.81 g (77%) of the title compound as a pale yellow solid which was not further purified. [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.79 (s, 1H), 7.78 (d, J=7.8 Hz, 1H), 7.53-7.58 (m, 2H), 7.31-7.39 (m, 2H), 4.22 (dt, J=13.5, 4.4 Hz, 2H), 3.37-3.49 (m, 2H), 3.06-3.15 (m, 2H), 1.91-2.05 (m, 2H), 1.75-1.83 (m, 2H), 1.65-1.75 (m, 2H), 1.44-1.55 (m, 2H); LCMS RtB=2.80 min, [M+H]+=297.2].

후처리

  1. customwas placed in a microwave tube
  2. customThe tube was sealed
  3. filtrationThe mixture was filtered
  4. washthe residue washed with ethanol
  5. concentrationThe filtrate was concentrated
  6. filtrationthe precipitate filtered
  7. washwashed with ethanol
  8. dissolutionThe combined solid material was dissolved in ethyl acetate
  9. washwashed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2c3365bfdad04b4d927b0e6172fba61b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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