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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
ノート
印刷プレビュー

反応式

HRID 729502 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 102145106-(Bromomethyl)quinoxalineHCID 57832787HCID 57832787、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4193c67cc9d243f9a3c2af1b3b88c574
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582636B2

反応ノート

読み込み中…

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