Sodium Sulfite → 3-((2-(Methylsulfinyl)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-b]pyridazine-6-carbonitrile

HRID 1848253노트

반응식

HRID 1848253 반응식
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][C:13]3[N:17]4[N:18]=[C:19]([C:22]#[N:23])[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][C:13]3[N:17]4[N:18]=[C:19]([C:22]#[N:23])[CH:20]=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)=[O:32]

참가 물질

5

반응물 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 866812263-((2-(Methylthio)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-b]pyridazine-6-carbonitrile

생성물 1

HCID 866812283-((2-(Methylsulfinyl)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-b]pyridazine-6-carbonitrile수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 3-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-b]pyridazine-6-carbonitrile (0.7 g, 2.1 mmol) in DCM (30 mL) at 0° C. was slowly added m-CPBA (0.4 g, 2.1 mmol). The reaction mixture was stirred at 0° C. for 2 h, then aq Na2SO3 (25 mL) was added and the mixture was stirred for 0.5 h. The organic layer was separated and dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 50:1 to 20:1 DCM/MeOH to afford 3-((2-(methylsulfinyl)benzo[d]thiazol-6-yl)methyl)imidazo[1,2-b]pyridazine-6-carbonitrile as a yellow solid (0.7 g, 96%). 1H NMR (300 MHz, CDCl3) δ 8.11 (d, J=9.3 Hz, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.92 (s, 1H), 7.82 (s, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.31 (d, J=9.3 Hz, 1H), 4.54 (s, 2H), 3.07 (s, 3H). LCMS (ESI) m/z 354 (M+H)+.

후처리

  1. customat 0° C.
  2. stirringthe mixture was stirred for 0.5 h
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 50:1 to 20:1 DCM/MeOH

출처 및 근거

ORD 기록
ord-2b7e44685ecd48f98e569e72415965fe
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952058B2

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