Trimethylsilyl iodide → 2-bromo-8-(((3S,4S)-4-(fluoromethyl)pyrrolidin-3-yl)amino)imidazo[1,2-b]pyridazine-7-carboxamide, hydroiodide

HRID 1487332Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][C@H:11]3[C@@H:15]([CH2:16][F:17])[CH2:14][N:13](C(OCC4C=CC=CC=4)=O)[CH2:12]3)=[C:8]([C:28](=[O:30])[NH2:29])[CH:7]=[N:6][N:5]2[CH:31]=1.[I:32][Si](C)(C)C>C(#N)C>[IH:32].[Br:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][C@H:11]3[C@@H:15]([CH2:16][F:17])[CH2:14][NH:13][CH2:12]3)=[C:8]([C:28]([NH2:29])=[O:30])[CH:7]=[N:6][N:5]2[CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of (3S,4S)-benzyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate (240 mg, 0.488 mmol) in acetonitrile (3 ml) at 0° C. was added iodotrimethylsilane (0.266 ml, 1.954 mmol) dropwise. The reaction mixture was stirred at 0° C. for 10 min and at room temperature for 1.5 h. The reaction was cooled to 0° C. and quenched with MeOH (2 ml). The resulting suspension was stirred at 0° C. for 30 min, filtered, washed with ethyl ether, and dried under vacuum to afford 2-bromo-8-(((3S,4S)-4-(fluoromethyl)pyrrolidin-3-yl)amino)imidazo[1,2-b]pyridazine-7-carboxamide, hydroiodide as an off-white solid. ESI-MS (analytical LCMS Method A): m/z 357.0 ([M+H]+).

Workup

temperatureThe reaction was cooled to 0° C.
customquenched with MeOH (2 ml)
stirringThe resulting suspension was stirred at 0° C. for 30 min
filtrationfiltered
washwashed with ethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-e572d3d8a5fe4ad6860c6e3817cf70ce
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428511B2

Reaction notes

Loading…