1-Butanol → HCID 57929960, compound

HRID 1929975Notes

Reaction equation

HRID 1929975 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]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=2[F:24])=[CH:4][CH:3]=1.C(O)CCC.O.[NH2:31][NH2:32]>O.CCOC(C)=O>[NH:31]([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]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=2[F:24])=[CH:4][CH:3]=1)[NH2:32]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 24654Hydrazine hydrate (1:1)HCID 57929967HCID 57929967, compound

Product 1

HCID 57929960HCID 57929960, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 5-(6-chloropyridazin-3-yl)-6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole (0.25 g, 0.71 mmol; prepared using General Procedure H from 3,6-dichloropyridazine followed by General Procedure I from 5-iodo-6-(2,4,5-trifluorophenyl)imidazo[2,1-b]oxazole [Example #7, step C]) and n-butanol (2.0 mL) to give a tan suspension. Water (1.0 mL) was added, followed by hydrazine hydrate (0.42 mL, 8.6 mmol). The resulting mixture was heated at about 100° C. for about 20 h. To the cooled reaction mixture were added EtOAc and water and the layers were separated. The aqueous solution was extracted with EtOAc (2×50 mL) and the combined organic extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound (0.19 g, 77%): LC/MS (Table 1, Method b) Rt=1.58 min; MS m/z 347.1 (M+H)+.

Workup

  1. customto give a tan suspension
  2. customTo the cooled reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous solution was extracted with EtOAc (2×50 mL)
  5. dry with materialthe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-5d4e4382f2e445b0ba14b417a7a4573d
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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