Diisopropylethylamine → N-[[5-tert-butyl-2-(3-chlorophenyl)-2H-pyrazol-3-yl]-methyl]-2-(3-fluoro-4-methylsulfonyl-phenyl)propionamide

HRID 1843007Notes

Reaction equation

HRID 1843007 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([C:12]2[CH:17]=[CH:16][C:15](F)=[C:14]([Cl:19])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC(N(C)C)=C(C)C.[F:28][C:29]1[CH:30]=[C:31]([CH:39]([CH3:43])[C:40](O)=[O:41])[CH:32]=[CH:33][C:34]=1[S:35]([CH3:38])(=[O:37])=[O:36].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:40](=[O:41])[CH:39]([C:31]2[CH:32]=[CH:33][C:34]([S:35]([CH3:38])(=[O:36])=[O:37])=[C:29]([F:28])[CH:30]=2)[CH3:43])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:19])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 66644105(3-tert-butyl-1-(3-chloro-4-fluorophenyl)-1H-pyrazol-5-yl)methanamineHCID 708157452-(3-Fluoro-4-(methylsulfonyl)phenyl)propanoic acid

Product 1

HCID 49802516N-[[5-tert-butyl-2-(3-chlorophenyl)-2H-pyrazol-3-yl]-methyl]-2-(3-fluoro-4-methylsulfonyl-phenyl)propionamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-tert-butyl-1-(3-chloro-4-fluorophenyl)-1H-pyrazol-5-yl)methanamine (49 mg, 0.189 mmol) in DCM (1.3 mL) at room temperature and under nitrogen atmosphere was added 1-chloro-N,N,2-trimethyl-1-propenylamine (48 μL, 0.369 mmol), After 1 h of stirring were added 2-(3-fluoro-4-(methylsulfonyl)phenyl)propanoic acid (93 mg, 0.378 mmol) and N-ethyldiisopropylamine (0.11 mL, 0.662 mmol). The reaction mixture was stirred overnight at room temperature, washed with NaHCO3 solution (2×10 mL), dried over sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by column chromatography (eluent: ethyl acetate/cyclohexane (2:1)) to give pure N-[[5-tert-butyl-2-(3-chlorophenyl)-2H-pyrazol-3-yl]-methyl]-2-(3-fluoro-4-methylsulfonyl-phenyl)-propionamide (example compound D1) (66 mg, 71%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. washwashed with NaHCO3 solution (2×10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by column chromatography (eluent: ethyl acetate/cyclohexane (2:1))

Sources & evidence

ORD record
ord-db17c32d6a054c7aa84dc01d55bd0ce3
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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