1,2-Dichloroethane → (4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

HRID 1941884Notes

Reaction equation

HRID 1941884 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[CH:9]=[N:8]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.O[NH:43][C:44](=[NH:53])[C:45]1[CH:50]=[CH:49][C:48]([CH2:51][OH:52])=[CH:47][CH:46]=1.Cl>CN(C=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]2[O:18][N:53]=[C:44]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][OH:52])=[CH:47][CH:46]=3)[N:43]=2)[CH:9]=[N:8]1

Participants

9

Reactant 6

HCID 111,2-Dichloroethane2×HCID 313Hydrochloric AcidHCID 757711-Hydroxybenzotriazole2×HCID 81531Diisopropylethylamine2×HCID 167877231-(2-Pyridinyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 178513316HCID 178513316, compound

Product 1

HCID 66996907(4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanolYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (2.57 g, 9.99 mmol) in DMF (30 mL) was added EDC (2.395 g, 12.49 mmol), HOBt (1.913 g, 12.49 mmol) and Hunig's Base (5.24 mL, 30.0 mmol). The reaction was stirred for 40 min. at room temperature, then N-hydroxy-4-(hydroxymethyl)benzimidamide, Int.2, (2.076 g, 12.49 mmol) was added. The reaction mixture was stirred at room temperature for 7 h, then additional EDC (2.395 g, 12.49 mmol), HOBt (1.913 g, 12.49 mmol) and Hunig's Base (5.24 mL, 30.0 mmol) were added. The reaction was heated to 60° C. for 2 h, then at 110° C. for 10 min. 1N aq. HCl was added to adjust the pH to 1, then 30 mL of water was added. The resulting precipitated product was collected by filtration and washed with water to afford (4-(5-(1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (2.28 g, 5.83 mmol, 58%) as a light yellow solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 7 h
  2. temperatureThe reaction was heated to 60° C. for 2 h
  3. waitat 110° C. for 10 min
  4. customThe resulting precipitated product
  5. filtrationwas collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-8051eedff57d4b2a9774cd314f2cbe34
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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