Chloroform → N-(6-(6-Chloro-5-(methylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162453Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([CH:14]=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23].C(Cl)(Cl)Cl.[I:30]N1C(=O)CCC1=O.C(Cl)Cl>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([I:30])=[C:15]([NH:17][C:18](=[O:20])[CH3:19])[N:16]=3)[N:13]=2)=[CH:4][C:3]=1[NH:21][S:22]([CH3:25])(=[O:23])=[O:24]

Participants

Conditions

Temperature: 25 °C

Procedure

To a 50 mL round-bottomed flask was added N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (Example 19) (0.404 g, 1.06 mmol), chloroform (20 mL) and N-iodosuccinimide (0.48 g, 2.1 mmol). The mixture was stirred at 25° C. for 1 h then poured into CH2Cl2 (200 mL) and water (200 mL). The solution contained a precipitate. This was filtered and the filtercake was washed with water and then dried under vacuum. The solid was taken up in MeOH/CH2Cl2 and concentrated onto Celite® (diatomaceous earth). Purification by silica gel chromatography (2.0 to 10% MeOH/CH2Cl2) afforded the title compound as a yellow solid (0.199 g, 37%). MS (ESI, positive ion) m/z: 506.4 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.07 (s, 3H), 3.20 (s, 3H), 7.96 (d, J=9.6 Hz, 1H), 8.20 (d, J=9.4 Hz, 1H), 8.55 (d, J=2.2 Hz, 1H), 8.98 (d, J=2.2 Hz, 1H), 9.98 (s, 1H), 10.13 (s, 1H).

Workup

filtrationThis was filtered
washthe filtercake was washed with water
customdried under vacuum
concentrationconcentrated onto Celite® (diatomaceous earth)
customPurification by silica gel chromatography (2.0 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-3f8393ba551d4ba3802ae0155d9e64e3
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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