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

HRID 1941890Notes

Reaction equation

HRID 1941890 reaction equation
[C:1]1([N:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[NH:34][C:35](=[NH:44])[C:36]1[CH:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][CH:37]=1>CN(C=O)C.O>[C:1]1([N:7]2[C:11]([C:12]([F:13])([F:14])[F:15])=[C:10]([C:16]3[O:18][N:44]=[C:35]([C:36]4[CH:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][CH:37]=4)[N:34]=3)[CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 6886991-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 178513316HCID 178513316, compound

Product 1

HCID 66996273(4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (2 g, 7.81 mmol), HOBT (1.315 g, 8.59 mmol) and EDC (1.646 g, 8.59 mmol) were dissolved in DMF (18 mL) under nitrogen at room temperature. The resulting clear, pale yellow solution was stirred for 20 minutes, then N-hydroxy-4-(hydroxymethyl)benzimidamide, Int.2, (1.297 g, 7.81 mmol) was added in several portions. The reaction was placed in an oil bath preheated to 140° C. for 10 hours. The reaction was cooled to room temperature, poured into water (150 mL), stirred vigorously and placed in a sonicator bath for 1 hour. The solids were collected by filtration, washed with water, air dried and then placed under vacuum to give (4-(5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (2.5 g, 6.47 mmol) as a very light yellow solid. The compound had an HPLC retention time=3.76 min.−Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1=387.1 1H NMR (500 MHz, MeOD) δ ppm 4.70 (s, 2H), 7.53-7.57 (m, 4 H), 7.57-7.62 (m, 1H), 7.61 (d, J=6.4 Hz, 2H), 8.12 (d, J=8.2 Hz, 2H), 8.48 (s, 1H).

Workup

  1. customThe reaction was placed in an oil bath
  2. waitpreheated to 140° C. for 10 hours
  3. stirringstirred vigorously
  4. waitplaced in a sonicator bath for 1 hour
  5. filtrationThe solids were collected by filtration
  6. washwashed with water, air
  7. customdried

Sources & evidence

ORD record
ord-e050e823c1cb455bacbd902ac28f6237
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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