6-[3-(2-Chloromethyl-3-methylpyridin-4-ylsulfanyl)propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine → HCID 18799445, compound

HRID 1637645Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[N:5]=[C:4]([SH:9])[N:3]=1.[Cl:10][CH2:11][C:12]1[C:17]([CH3:18])=[C:16]([S:19][CH2:20][CH2:21][CH2:22][S:23][C:24]2[CH:25]=[CH:26][C:27]3[N:28]([C:30]([N+:33]([O-:35])=[O:34])=[CH:31][N:32]=3)[N:29]=2)[CH:15]=[CH:14][N:13]=1>CC(O)C>[ClH:10].[CH3:18][C:17]1[C:12]([CH2:11][S:9][C:4]2[N:5]=[C:6]([NH2:8])[CH:7]=[C:2]([NH2:1])[N:3]=2)=[N:13][CH:14]=[CH:15][C:16]=1[S:19][CH2:20][CH2:21][CH2:22][S:23][C:24]1[CH:25]=[CH:26][C:27]2[N:28]([C:30]([N+:33]([O-:35])=[O:34])=[CH:31][N:32]=2)[N:29]=1

Participants

Conditions

Temperature: 4 °C

Procedure

A suspension of 4,6-diamino-pyrimidine-2-thiol (0.36 g, 2.5 mmol) and 6-[3-(2-chloromethyl-3-methyl-pyridin-4-ylsulfanyl)-propylsulfanyl]-3-nitroimidazo[1,2-b]pyridazine (1.03 g, 2.5 mmol) in 2-propanol (50 ml) is heated under reflux for 6 h under a nitrogen atmosphere. After cooling to 4° C., the precipitate is filtered, washed with cold 2-propanol and dried in vacuo. The crude product is triturated with hot acetonitrile (15 ml), filtered and dried again in vacuo to give the title compound as an off-white solid, 1.25 g (90%). M.p. 215-224° C.

Workup

temperatureis heated
temperatureunder reflux for 6 h under a nitrogen atmosphere
filtrationthe precipitate is filtered
washwashed with cold 2-propanol
customdried in vacuo
customThe crude product is triturated with hot acetonitrile (15 ml)
filtrationfiltered
customdried again in vacuo

Sources & evidence

ORD record: ord-ee26a7b4500540409074da0cfd6db4cb
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043242

Reaction notes

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