1-Propanol → 6-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazole

HRID 1930094Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[N:15]3[C:11]([O:12][CH:13]=[CH:14]3)=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])=[CH:4][CH:3]=1.C(O)CC.O.[NH2:29][NH2:30]>C(Cl)Cl>[F:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[C:9]1[N:10]=[C:11]2[N:15]([C:8]=1[C:5]1[N:6]=[N:7][C:2]([NH:29][NH2:30])=[CH:3][CH:4]=1)[CH:14]=[CH:13][O:12]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask was added 5-(6-chloropyridazin-3-yl)-6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole (4.00 g, 12.0 mmol), 1-propanol (80 mL) and hydrazine hydrate (5.89 mL, 120 mmol). The reaction mixture was heated at about 100° C. for about 20 h. The reaction mixture was cooled to ambient temperature and then diluted with DCM (100 mL). The organic layer was washed with saturated aqueous NaHCO3 (80 mL), dried with MgSO4, filtered and concentrated under reduced pressure to give the title compound (3.04 g, 77%) as a solid. LC/MS (Table 1, Method g) Rt=1.58 min; MS m/z: 329.1 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
washThe organic layer was washed with saturated aqueous NaHCO3 (80 mL)
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3330a315e55d4007b0a0d66b6af305ea
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

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