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

HRID 1930094
Notes
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Reaction equation

HRID 1930094 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10311-PropanolHCID 24654Hydrazine hydrate (1:1)HCID 579298665-(6-Chloropyridazin-3-yl)-6-(2,4-difluorophenyl)imidazo[2,1-b]oxazole

Product 1

HCID 579298696-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazoleYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

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

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washThe organic layer was washed with saturated aqueous NaHCO3 (80 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes