Triethylamine → HCID 67183996, compound

HRID 45830Notes

Reaction equation

HRID 45830 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[N:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([C:33]3[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=3)[CH2:36][NH2:37])=[N:22][N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[N:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21]([C:33]3[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=3)[CH2:36][NH:37][C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)=[N:22][N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:30])[CH3:31])[CH:24]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 67184148HCID 67184148, compound

Product 1

HCID 67183996HCID 67183996, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Trifluoromethylbenzoylchloride (0.054 g, 0.26 mmol) was added to a solution of 3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzylamine (0.10 g, 0.26 mmol) (prepared as described in Example 17) and triethylamine (0.08 g, 0.79 mmol) in dry DCM (2.0 ml) at 0° C. The reaction mixture was stirred at room temperature under nitrogen atmosphere for 6 h. The organic layer was washed with water (2.0 mL) and dried over Na2SO4. The filtrate was evaporated to dryness to give an oil which was purified by flash chromatography, over silica gel, using dichloromethane/MeOH (98:0.2) as eluent, to afford N-{3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzyl}-4-trifluoromethyl-benzamide (0.110 g, 0.20 mmol, 76%).

Workup

  1. washThe organic layer was washed with water (2.0 mL)
  2. dry with materialdried over Na2SO4
  3. customThe filtrate was evaporated to dryness
  4. customto give an oil which
  5. customwas purified by flash chromatography, over silica gel

Sources & evidence

ORD record
ord-385c1de91a3f48d0970397ea31e30384
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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