Dimethyl Sulfoxide → HCID 56928278, compound

HRID 1773632Notes

Reaction equation

[CH2:1]([NH:5][C:6]1[C:7]2[N:8]([C:18]([C:21]3[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=3)=[CH:19][N:20]=2)[N:9]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:11]=1)[CH:2]([CH3:4])[CH3:3].[S].[CH:30]1([NH2:33])[CH2:32][CH2:31]1.C[S:35](C)=O>>[CH:30]1([NH:33][C:25]([C:24]2[CH:27]=[CH:28][C:21]([C:18]3[N:8]4[N:9]=[C:10]([C:12]5[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=5)[CH:11]=[C:6]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])[C:7]4=[N:20][CH:19]=3)=[CH:22][CH:23]=2)=[S:35])[CH2:32][CH2:31]1

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 69828Cyclopropylamine

HCID 5362487Sulfur

HCID 86705348HCID 86705348, compound

Product 1

HCID 56928278HCID 56928278, compoundYield 10%

Conditions

Temperature: 100 °C

Procedure

A mixture of 40 mg (108 μmol) 4-[8-(isobutylamino)-6-(pyridin-4-yl)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde which was prepared according to intermediate example 13a, 3.45 mg sulfur, 37 μL cyclopropanamine and 250 μL dimethyl sulfoxide were heated at 100° C. under microwave irradiation for 4 hours. The mixture was stirred at 90° C. overnight, the solvent was evaporated and the residue purified by chromatography to give 4.8 mg (10%) of the title compound.

Workup

customwas prepared
customthe solvent was evaporated
customthe residue purified by chromatography

Sources & evidence

ORD record: ord-e89735e8072841dcb0126564e80859b4
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255100B2

Reaction notes

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