Dichloromethane → HCID 118432072, compound

HRID 2208053Notes

Reaction equation

HRID 2208053 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH:19]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)=[CH:22][CH:21]=2)[CH2:18][C:17]([C:32]([C:38]([F:41])([F:40])[F:39])([C:34]([F:37])([F:36])[F:35])[OH:33])=[N:16]1.C(N(CC)CC)C.C(Cl)(=O)C.ClCCl>O>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[CH:19]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH2:27][CH2:28][N:29]([C:3](=[O:4])[CH3:2])[CH2:30][CH:31]=3)=[CH:24][CH:25]=2)[CH2:18][C:17]([C:32]([C:38]([F:41])([F:39])[F:40])([C:34]([F:35])([F:36])[F:37])[OH:33])=[N:16]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 118431833HCID 118431833, compound

Product 1

HCID 118432072HCID 118432072, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Chloro-phenyl)-5-[4-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate (15.0 mg, 0.02 mmol) prepared in Example 292, triethylamine (9.3 uL, 0.07 mmol) and acetyl chloride (3.6 uL, 0.03 mmol) were added at 0° C. to dichloromethane (1.0 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 1N hydrochloric acid, 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=1/3) to give 4.9 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 1N hydrochloric acid
  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=1/3)

Sources & evidence

ORD record
ord-d00a0c48c00f470297361d089eec39a5
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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