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Diisopropylethylamine → 6-{4-[2-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyridin-5-yl]-piperazin-1-ylmethyl}-quinoxaline

HRID 729502
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HRID 729502 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[N:14]3[CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[N:31]2.C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[CH2:24][CH2:23][N:22]([CH2:27][C:28]5[CH:29]=[C:30]6[C:35](=[CH:36][CH:37]=5)[N:34]=[CH:33][CH:32]=[N:31]6)[CH2:21][CH2:20]4)[N:14]3[CH:25]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 102145106-(Bromomethyl)quinoxalineHCID 57832787HCID 57832787, 화합물

생성물 1

HCID 119613066-{4-[2-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyridin-5-yl]-piperazin-1-ylmethyl}-quinoxaline수율 29.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

2-(4-tert-Butyl-phenyl)-5-piperazin-1-yl-imidazo[1,2-a]pyridine (0.086 g, 0.258 mmol) was dissolved in DMSO (1 mL) and treated with 6-bromomethyl-quinoxaline (0.072 g, 0.323 mmol) followed by diisopropylethylamine (0.046 mL, 0.258 mmol). The mixture was stirred at room temperature overnight and diluted with ethyl acetate (10 mL). The solution was washed with water and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the crude product. Purification by flash silica gel chromatography (40-50% acetone/hexanes) gave 0.0362 g (29%) of the title compound. HPLC (Method B): r.t.=9.6 min., purity 100% at 210-370 nm, 96.0% at 238 nm. HRMS: calcd for C30H32N6+H+, 477.27612; found (ESI, [M+H]+), 477.2786.

후처리

  1. washThe solution was washed with water and saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield the crude product
  6. customPurification by flash silica gel chromatography (40-50% acetone/hexanes)

출처 및 근거

ORD 기록
ord-4193c67cc9d243f9a3c2af1b3b88c574
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07582636B2

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