HCID 118431652, compound → HCID 118431993, compound

HRID 2208045Notes

Reaction equation

HRID 2208045 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])[N:19]=[C:18]([C:28]([C:34]([F:37])([F:36])[F:35])([C:30]([F:33])([F:32])[F:31])[OH:29])[CH2:17]3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[CH3:38][Mg]Cl>O1CCCC1>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH:16]([C:12]2[CH:11]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([OH:3])([CH3:38])[CH3:2])[CH:5]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:17][C:18]([C:28]([C:34]([F:37])([F:36])[F:35])([C:30]([F:31])([F:32])[F:33])[OH:29])=[N:19]1

Participants

4

Reactant 2

HCID 118431652HCID 118431652, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 118431993HCID 118431993, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of 5-(3′-acetyl-biphenyl-3-yl)-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (39.0 mg, 0.07 mmol) prepared in Example 224 in tetrahydrofuran (1.0 mL), was slowly added methylmagnesium chloride (in 3.0 M tetrahydrofuran, 120.0 uL, 0.36 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred at −78° C. for 5 hours, quenched with a saturated solution of ammonium chloride at 0° C., and then extracted with ethyl acetate. The extract was washed with distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3) to give 20.0 mg of the titled compound as a yellow liquid.

Workup

  1. customat −78° C
  2. customquenched with a saturated solution of ammonium chloride at 0° C.
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow liquid residue
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)

Sources & evidence

ORD record
ord-f5cdd078c675446f9a140f60974c0ff3
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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