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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
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HRID 69257 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 57917414HCID 57917414, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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®

출처 및 근거

ORD 기록
ord-95433c3188094d37aaa552ee089c6dc6
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822468B2

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