Pyridine → HCID 118431871, compound

HRID 2208054Notes

Reaction equation

HRID 2208054 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])[N:17]=[C:16]([C:26]([C:32]([F:35])([F:34])[F:33])([C:28]([F:31])([F:30])[F:29])[OH:27])[CH2:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:42](Cl)(=[O:44])[CH3:43].ClCCl>O>[NH:1]([C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])[N:17]=[C:16]([C:26]([C:32]([F:35])([F:34])[F:33])([C:28]([F:29])([F:30])[F:31])[OH:27])[CH2:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)[C:42]([CH3:43])=[O:44]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 118431775HCID 118431775, compound

Product 1

HCID 118431871HCID 118431871, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3′-Amino-biphenyl-4-yl)-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (8.0 mg, 0.02 mmol) prepared in Example 253, pyridine (2.2 uL, 0.02 mmol) and acetyl chloride (1.4 uL, 0.02 mmol) were added at 0° C. to dichloromethane (0.3 mL). The reaction mixture was stirred at room temperature for 2 hours and then distilled water was added thereto. The reaction mixture was extracted with dichloromethane two times. The combined extract was washed with a 1N hydrochloric acid solution, a saturated solution of sodium carbonate, 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=1/1) to give 1.9 mg of the titled compound as a yellow liquid.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane two times
  2. extractionThe combined extract
  3. washwas washed with a 1N hydrochloric acid solution
  4. dry with materiala saturated solution of sodium carbonate, and brine, dried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-7f182274ae394e6095191821f7332bd4
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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