N-Iodosuccinimide → HCID 68839933, 화합물

HRID 1432657노트

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HRID 1432657 반응식
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[O:22][CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1C(=O)N([I:31])C(=O)C1>CC#N>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][C:19]([I:31])=[CH:20][C:21]=3[O:22][CH3:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

참가 물질

4

반응물 2

HCID 120273N-IodosuccinimideHCID 57932986HCID 57932986, 화합물

생성물 1

HCID 68839933HCID 68839933, 화합물수율 88%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 8-(1-ethyl-propyl)-3-(3-methoxy-thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.75 g, 2.28 mmol) and CH3CN (10 mL) is added NIS (0.54 g, 2.39 mmol). The solution is stirred overnight, concentrated, diluted with EtOAc (30 mL), washed with water (30 mL), sat. NH4Cl (30 mL), 20% (NaHSO3) (30 mL), brine (30 mL), dried over MgSO4, filtered and concentrated. The residue is purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient) furnish the title compound (0.91 g, 2.00 mmol, 88%). 1H NMR (CDCl3) δ 0.85 (t, J=7.5 Hz, 6H), 1.71-1.89 (m, 4H), 2.46 (s, 3H), 2.52 (s, 3H), 3.25-3.35 (m, 1H), 3.83 (s, 3H), 6.64 (s, 1H), 7.12 (s, 1H). LC/MS (m/z): calcd. for C18H22IN3OS (M+H)+: 456.4; found: 456.0.

후처리

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (30 mL)
  3. washwashed with water (30 mL), sat. NH4Cl (30 mL), 20% (NaHSO3) (30 mL), brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by ISCO column chromatography (15%-20% EtOAc/hexane gradient)

출처 및 근거

ORD 기록
ord-70cd8e4ded6b45729caca18bc5a46bb0
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612067B2

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