Calcium Carbonate → HCID 25020125, compound

HRID 561248Notes

Reaction equation

HRID 561248 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])[O:10]1.C(=O)([O-])[O-].[Ca+2].[NH:24]1[CH:28]=[C:27](/[CH:29]=[CH:30]/[C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)[CH:26]=[N:25]1>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:10])([CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C@H:11]([N:24]1[CH:28]=[C:27](/[CH:29]=[CH:30]/[C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)[CH:26]=[N:25]1)[CH3:12]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 66999641HCID 66999641, compound

Product 1

HCID 25020125HCID 25020125, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(((2R,3S)-2-(2,4-difluorophenyl)-3-methyl oxiran-2-yl)methyl)-1H-1,2,4-triazol obtained in step 3 (55.9 mg) was suspended in N,N-dimethylformamide (1.6 mL), and calcium carbonate (41.9 mg) and 4-((E)-2-(1H-pyrazol-4-yl)vinyl)benzonitrile (39.5 mg) were added thereto. The mixture was stirred at room temperature for 20 minutes under an argon atmosphere, and reacted by microwave irradiation at 180° C. for 15 minutes. After completion of the reaction, the resulting mixture was extracted with ethyl acetate (10 mL) and the extract was washed successively with saturated amoniumchloride (10 mL) and brine (10 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated by evaporation under a reduced pressure. The resulting residue was purified by silica gel chromatography to obtain the title compound (0.039 g, yield 43.5%).

Workup

  1. customreacted by microwave irradiation at 180° C. for 15 minutes
  2. customAfter completion of the reaction
  3. extractionthe resulting mixture was extracted with ethyl acetate (10 mL)
  4. washthe extract was washed successively with saturated amoniumchloride (10 mL) and brine (10 mL)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under a reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-19e3b190747d40c78ca97a36711952b0
Source dataset
uspto-grants-2011_11
Patent number
US08063229B2

Reaction notes

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