Ethylene Glycol → HCID 46833530, compound

HRID 1848334Notes

Reaction equation

P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH:19]1([C:22]2[N:33]=[C:25]3[C:26]([O:31][CH3:32])=[CH:27][CH:28]=[C:29](I)[N:24]3[N:23]=2)[CH2:21][CH2:20]1>[Cu](I)I.CC(O)C>[CH:19]1([C:22]2[N:33]=[C:25]3[C:26]([O:31][CH3:32])=[CH:27][CH:28]=[C:29]([N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[N:24]3[N:23]=2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

Copper iodide (1.0 mg, 0.005 mmol) and potassium phosphate (42.5 mg, 0.200 mmol), kept under argon, was added 2-propanol (200 μL), ethylene glycol (12.4 mg, 0.200 mmol), piperidine (10.1 mg, 0.12 mmol) and 2-cyclopropyl-5-iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine (31.5 mg, 0.100 mmol). The resulting suspension was heated to 80° C. for 4 days. The mixture was allowed to reach room temperature before it was extracted with dichloromethane (3 mL). The organic phase was washed with brine, dried (Na2SO4) and filtered before it was concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in toluene to 40% EtOAc in toluene) to give 2-cyclopropyl-8-methoxy-5-piperidin-1-yl-[1,2,4]triazolo[1,5-a]pyridine (2.2 mg.

Workup

customto reach room temperature before it
extractionwas extracted with dichloromethane (3 mL)
washThe organic phase was washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered before it
concentrationwas concentrated in vacuo
customThe crude product was purified by flash column chromatography (SiO2, 20% EtOAc in toluene to 40% EtOAc in toluene)

Sources & evidence

ORD record: ord-60882cb43d2d4777a642e9e8d153e5b9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952162B2

Reaction notes

Loading…