Diethyl Ether → 3-{2,6-Dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazin-8-yl}-pentan-3-ol

HRID 1432615노트

반응식

HRID 1432615 반응식
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10](=[O:13])[CH2:11][CH3:12])=[CH:8][C:7]([CH3:14])=[N:6][N:5]2[C:15]=1[C:16]1[S:17][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=2)=[CH:19][C:20]=1[CH3:21].[CH3:29][CH2:30]OCC.C([Mg]Br)C>CCOC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([C:10]([OH:13])([CH2:29][CH3:30])[CH2:11][CH3:12])=[CH:8][C:7]([CH3:14])=[N:6][N:5]2[C:15]=1[C:16]1[S:17][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=2)=[CH:19][C:20]=1[CH3:21]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 688400841-{2,6-Dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazin-8-yl}-propan-1-oneHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 688404123-{2,6-Dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazin-8-yl}-pentan-3-ol수율 37%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a −0° C. solution of 1-{2,6-dimethyl-3-[3-methyl-5-(6-methyl-pyridin-2-yl)-thiophen-2-yl]-imidazo[1,2-b]pyridazin-8-yl}-propan-1-one (0.040 g, 0.10 mmol) and Et2O (5 mL) is added 3.0 M ethyl magnesium bromide (0.68 mL, 2.05 mmol). The solution is warmed to ambient temperature, diluted with EtOAc (30 mL) washed with sat. NH4Cl (20 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (20%-30% EtOAc/hexane gradient) furnish the title compound (0.016 g, 0.038 mmol, 37%). 1H NMR (CDCl3), δ 0.89 (t, J=7.4 Hz, 6H), 1.92-2.01 (m, 4H), 2.14 (s, 3H), 2.46 (s, 3H), 2.53 (s, 3H), 3.57 (s, 3H), 6.39 (s, 1H), 6.66 (s, 1H), 7.01 (d, J=7.5 Hz, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.52 (s, 1H), 7.57 (dd, J=7.9, 7.5 Hz, 1H). LC/MS (m/z): calcd. for C24H28N4OS (M+H)+: 421.3; found: 421.3.

후처리

  1. washwashed with sat. NH4Cl (20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by ISCO column chromatography (20%-30% EtOAc/hexane gradient)

출처 및 근거

ORD 기록
ord-7643a38aa7884ffc887861b63c33124f
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612067B2

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