Sodium Sulfite → 6-((6-Methoxyimidazo[1,2-b]pyridazin-3-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole

HRID 1848165Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-((6-methoxyimidazo[1,2-b]pyridazin-3-yl)methyl)-2-(methylthio)benzo[d]thiazole (500 mg, 1.46 mmol) in DCM (30 mL) was added m-CPBA (314 mg, 1.82 mmol) at 0° C. The reaction mixture was stirred for 2 h at 0° C., then aq Na2SO3 (15 mL) was added and the mixture was stirred for 0.5 h. The organic layer was separated, 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 6-((6-methoxyimidazo[1,2-b]pyridazin-3-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole as a yellow solid (500 mg, 95%). 1H NMR (300 MHz, CDCl3) δ 7.99-7.93 (m, 2H), 7.76 (d, J=9.6 Hz, 1H), 7.53 (dd, J=1.5, 8.4 Hz, 1H), 7.46 (s, 1H), 6.65 (d, J=9.3 Hz, 1H), 4.42 (s, 2H), 3.94 (s, 3H), 3.06 (s, 3H). LCMS (ESI) m/z 359 (M+H)+.

Workup

stirringthe mixture was stirred for 0.5 h
customThe organic layer was separated
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with 50:1 to 20:1 DCM/MeOH

Sources & evidence

ORD record: ord-b7ec99ac52e04c1e9e8a125dd5ea4cfa
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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