Water → HCID 66879948, compound

HRID 1294508Notes

Reaction equation

Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[N:10]=[C:9]2[CH3:22])=[CH:6][CH:7]=1.Cl.[CH3:24][NH:25][CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Cl:21][C:17]1[CH:16]=[C:15]([C:14]#[C:13][C:11]2[N:10]=[C:9]([CH3:22])[N:8]([C:5]3[N:4]=[N:3][C:2]([N:25]([CH3:26])[CH3:24])=[CH:7][CH:6]=3)[CH:12]=2)[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 140 °C

Procedure

3-Chloro-6-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridazine (100 mg, 0.30 mmol) was dissolved in 2 mL dimethylforamide and dimethyl-amine hydrochloride (124 mg, 1.5 mmol) and cesium carbonate (396 mg, 1.2 mmol) were added. The reaction mixture was heated in the microwave at 140° C. for 60 min. After cooling to room temperature the reaction mixture was treated with 50 mL water and extracted three times with ethyl acetate (50 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude material was purified by flash chromatography (methylene chloride/methanol 100:0->90:10 gradient) and the desired product was obtained as a white solid (57 mg, 55%), MS: m/e=338.1 (M+H+).

Workup

temperatureAfter cooling to room temperature the reaction mixture
extractionextracted three times with ethyl acetate (50 mL each)
dry with materialThe combined organic extracts were dried with magnesium sulfate
filtrationfiltered
customevaporated
customThe crude material was purified by flash chromatography (methylene chloride/methanol 100:0->90:10 gradient)

Sources & evidence

ORD record: ord-481eed28bce44936899b57b9b368454e
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241760B2

Reaction notes

Loading…