Acetyl chloride → 5-[3-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole

HRID 2208049Notes

Reaction equation

HRID 2208049 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][CH:23]=[C:22]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)[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(Cl)(=O)C.C(N(CC)CC)C>ClCCl>[C:3]([N:29]1[CH2:28][CH:27]=[C:26]([C:22]2[CH:21]=[C:20]([CH:19]3[N:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[Cl:8])[N:16]=[C:17]([C:32]([C:38]([F:41])([F:39])[F:40])([C:34]([F:35])([F:36])[F:37])[OH:33])[CH2:18]3)[CH:25]=[CH:24][CH:23]=2)[CH2:31][CH2:30]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 1184319031-(2-chloro-phenyl)-5-[3-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate

Product 1

HCID 1184316935-[3-(1-acetyl-1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-1-(2-chloro-phenyl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazoleYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Chloro-phenyl)-5-[3-(1,2,3,6-tetrahydropyridin-4-yl)-phenyl]-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole trifluoroacetate (11.0 mg, 0.02 mmol) prepared in Example 230, acetyl chloride (1.5 uL, 0.02 mmol), and triethylamine (7.5 uL, 0.05 mmol) were added to dichloromethane (0.5 mL). The reaction mixture was stirred at room temperature for 1 hour, 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=1/1) to give 3.0 mg of the titled compound as a yellow liquid.

Workup

  1. washwashed with distilled water and brine
  2. dry with materialdried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow liquid residue
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-0c1008f3be3a4682b1ecc7a2741a5fff
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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