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Tetrahydrofuran → 2-((2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41544
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HRID 41544 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[N:11]1[CH2:22][CH2:21][C:14]2([C:19](=[O:20])[NH:18][CH2:17][CH2:16][CH2:15]2)[CH2:13][CH2:12]1.C1COCC1.Br[CH2:29][C:30]1[C:39]2[O:38][CH2:37][CH2:36][O:35][C:34]=2[CH:33]=[CH:32][CH:31]=1>[NH4+].[Cl-]>[O:35]1[CH2:36][CH2:37][O:38][C:39]2[C:30]([CH2:29][N:18]3[CH2:17][CH2:16][CH2:15][C:14]4([CH2:21][CH2:22][N:11]([C:2]5[CH:3]=[N:4][C:5]6[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=6)[N:1]=5)[CH2:12][CH2:13]4)[C:19]3=[O:20])=[CH:31][CH:32]=[CH:33][C:34]1=2
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5

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HCID 8028TetrahydrofuranHCID 153808895-(Bromomethyl)-2,3-dihydro-1,4-benzodioxineHCID 672517459-(Quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

생성물 1

HCID 532591132-((2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 79.9%

시약·촉매·용매 1

HCID 25517Ammonium Chloride
용매

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온도
50 °C

실험 절차

To a solution of 9-quinoxalin-2-yl-2,9-diaza-spiro[5.5]undecan-1-one (50 mg, 0.169 mmol) in THF (2 ml) sodium hydride 95% (6.07 mg, 0.253 mmol) was added and the mixture was stirred for 20 min. Then 5-bromomethyl-2,3-dihydro-benzo[1,4]dioxin (77 mg, 0.337 mmol) was added and the reaction mixture was heated at 50° C. over 18 h. Saturated aqueous NH4Cl solution (50 ml) was added and the reaction mixture was extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography (EtOAc/hexane 70:30) to yield 60 mg (79%) of the title compound. [1H NMR (600 MHz, DMSO-d6) δ 1.54-1.66 (2H, m) 1.76-1.84 (2H, m) 1.87-1.93 (2H, m) 2.02-2.12 (2H, m) 3.23 (2H, t) 3.39-3.47 (2H, m) 4.20-4.23 (2H, m) 4.24-4.27 (3H, m) 4.27-4.30 (1H, m) 4.41 (2H, s) 6.54 (1H, m) 6.72-6.75 (1H, m) 6.75-6.79 (1H, m) 7.32-7.41 (1H, m) 7.49-7.63 (2H, m) 7.80 (1H, d, J=8.07 Hz), 8.82 (1H, s), LCMS RtD=3.27 min, [M+H]+=445.2].

후처리

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified by flash chromatography (EtOAc/hexane 70:30)

출처 및 근거

ORD 기록
ord-25c1cb6dcce449658c29439c6e9a96ff
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530648B2

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