Triethylamine → HCID 66999762, compound

HRID 561243Notes

Reaction equation

HRID 561243 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([C@H:7]([CH3:24])[C@:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])([OH:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH:6]=1.C(N(CC)CC)C.[CH2:32]([O:34][CH:35]([O:38][CH2:39][CH3:40])[CH2:36]Br)[CH3:33]>CN(C)C=O>[CH2:32]([O:34][CH:35]([O:38][CH2:39][CH3:40])[CH2:36][NH:1][C:2]1[CH:3]=[N:4][N:5]([C@H:7]([CH3:24])[C@:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])([OH:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH:6]=1)[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 66999316HCID 66999316, compound

Product 1

HCID 66999762HCID 66999762, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R,3R)-3-(4-amino-1H-pyrazol-1-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol obtained in Step 2 (0.12 g, 0.35 mmol) was dissolved in N,N-dimethylformamide (2 mL) and triethylamine (0.058 g, 0.42 mmol) was slowly added thereto. The mixture was stirred at room temperature for 30 minutes, and bromoacetaldehyde diethyl acetal (0.065 mL, 0.42 mmol) was added thereto, followed by stirring at 80° C. for 4 hours. The reaction was terminated by adding ice water (0.1 mL) thereto. The resulting residue was extracted with ethyl acetate (20 mL), and the extract was washed successively with saturated ammonium chloride (20 mL) and brine (20 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 (0.071 g, yield 44%).

Workup

  1. stirringby stirring at 80° C. for 4 hours
  2. customThe reaction was terminated
  3. additionby adding ice water (0.1 mL)
  4. extractionThe resulting residue was extracted with ethyl acetate (20 mL)
  5. washthe extract was washed successively with saturated ammonium chloride (20 mL) and brine (20 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under a reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7ea04455219a440c91a20f0a9edaa140
Source dataset
uspto-grants-2011_11
Patent number
US08063229B2

Reaction notes

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