Sodium Iodide → HCID 136020103, compound

HRID 2279083Notes

Reaction equation

C[O:2][C:3]1[C:8]([C:9]2[N:13]3[N:14]=[C:15]([NH:18][C@@H:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:25](=[O:29])[CH2:26][C:27]#[N:28])[CH2:20]4)[CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.Cl[Si](C)(C)C.[I-].[Na+]>C(#N)C>[O:29]=[C:25]([N:21]1[CH2:22][CH2:23][CH2:24][C@@H:19]([NH:18][C:15]2[CH:16]=[CH:17][C:12]3[N:13]([C:9]([C:8]4[C:3](=[O:2])[NH:4][CH:5]=[CH:6][CH:7]=4)=[CH:10][N:11]=3)[N:14]=2)[CH2:20]1)[CH2:26][C:27]#[N:28]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-((3R)-3-{[3-(2-methoxypyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl]amino}piperidin-1-yl)-3-oxopropanenitrile (Preparation 3c, 58 mg, 0.15 mmol), chloro(trimethyl)silane (0.06 mL, 0.44 mmol) and sodium iodide (67 mg, 0.45 mmol) in acetonitrile (1.5 mL) was stirred at 80° C. for 50 minutes. The solvent was removed under reduced pressure and the residue was treated with water. The precipitate obtained was filtered, washed with more water and diethyl ether and dried in vacuo to give a solid that was purified by reverse phase chromatography (100% water to 1:1 water/(acetonitrile/methanol 1:1)) to yield the title compound (20 mg, 35%) as a solid.

Workup

customThe solvent was removed under reduced pressure
additionthe residue was treated with water
customThe precipitate obtained
filtrationwas filtered
washwashed with more water and diethyl ether
customdried in vacuo
customto give a solid
customthat was purified by reverse phase chromatography (100% water to 1:1 water/(acetonitrile/methanol 1:1))

Sources & evidence

ORD record: ord-07bcaac5974342e389a72ea32ca580d6
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133200B2

Reaction notes

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