Isobutyraldehyde → 6-[6-(2,4-Difluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine

HRID 1711786Notes

Reaction equation

HRID 1711786 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([NH:23][NH2:24])=[N:21][CH:22]=1)[CH:14]=[CH:13][O:12]2.[CH3:25][CH:26]([CH3:29])[CH:27]=O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:18]=[CH:19][C:20]3[N:21]([C:25]([CH:26]([CH3:29])[CH3:27])=[N:24][N:23]=3)[CH:22]=1)[CH:14]=[CH:13][O:12]2

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 12217721Iodo benzene diacetateHCID 594578146-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridin-3-yl)imidazo[2,1-b]oxazole

Product 1

HCID 594578236-[6-(2,4-Difluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridineYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a round bottom flask {5-[6-(2,4-difluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-pyridin-2-yl}-hydrazine (0.35 g, 1.1 mmol) and 2-methylpropionaldehyde (0.1 mL, 1.1 mmol) was dissolved in MeOH (5 mL) followed by heating to about 60° C. for about 1 h. The reaction was allowed to cool to ambient temperature and then iodobenzene diacetate (0.35 g, 1.1 mmol) was added followed by stirring for about 1 h. The reaction was then purified directly by flash chromatography using DCM/MeOH (90:10) as eluent followed by titration with Et2O to provide the title compound (0.075 g, 18%) as an off-white solid: LC/MS (Table 1, Method a) Rt, =2.12 min; MS m/z: 380.2 (M+H)+.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe reaction was then purified directly by flash chromatography

Sources & evidence

ORD record
ord-fc42c9a4a6f944888bdd262c8141b611
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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