Triethylamine → HCID 67183996, compound

HRID 1843618Notes

Reaction equation

HRID 1843618 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-eff1069ca40d4c04a390d0da1a408c7c
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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