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Triethylamine → 6-{6-[1-(2-Pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-imidazo[1,2-b]pyridazin-3-ylmethyl}-quinoline

HRID 69257
ノート
印刷プレビュー

反応式

HRID 69257 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH2:26][CH2:27]O)[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:29]([N:31](CC)[CH2:32][CH3:33])[CH3:30].S(Cl)(C)(=O)=O.N1CCCC1>C1COCC1.C(Cl)Cl>[N:31]1([CH2:27][CH2:26][N:24]2[CH:25]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]4[N:16]([C:12]([CH2:11][C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[N:1]=[CH:2][CH:3]=[CH:4]6)=[CH:13][N:14]=4)[N:17]=3)[CH:22]=[N:23]2)[CH2:32][CH2:33][CH2:30][CH2:29]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 57917414HCID 57917414、化合物

生成物 1

HCID 579173086-{6-[1-(2-Pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-yl]-imidazo[1,2-b]pyridazin-3-ylmethyl}-quinoline

試薬・触媒・溶媒 2

HCID 6344Dichloromethane
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-[4-(3-quinolin-6-ylmethyl-imidazo[1,2-b]pyridazin-6-yl)-pyrazol-1-yl]-ethanol (Example 210, 74 mg, 0.200 mmol), triethylamine (61 μL, 0.440 mmol) and mesylchloride (33 μL, 0.420 mmol) in THF (10 mL) was stirred at rt for 24 h. Pyrrolidine (6 eq.) was then added and the mixture was stirred at 60° C. for 48 h. The mixture was diluted with DCM and washed with NaHCO3 10% and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep® silica gel column, DCM/(MeOH+NH3)=95:5→80:20) to afford the title compound (tR 2.70 min (conditions 3), MH+=424.3)

後処理

  1. stirringthe mixture was stirred at 60° C. for 48 h
  2. washwashed with NaHCO3 10% and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (CombiFlash® Companion System®

出典と根拠

ORDレコード
ord-95433c3188094d37aaa552ee089c6dc6
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822468B2

反応ノート

読み込み中…

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