Triethylamine → 1-(2-Ethoxyphenyl)-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]prop-2-yn-1-one

HRID 2199182Notes

Reaction equation

HRID 2199182 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:26])[CH2:15][N:16]3[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[N:17]3)[CH2:10][CH2:9]2)[S:6][CH:7]=1)#[CH:2].[CH2:27]([O:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33])[CH3:28].C(N(CC)CC)C>O1CCCC1.[Pd](Cl)Cl.[Cu]I>[CH2:27]([O:29][C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](=[O:33])[C:2]#[C:1][C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:26])[CH2:15][N:16]3[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:23])([F:25])[F:24])=[N:17]3)[CH2:10][CH2:9]2)[S:6][CH:7]=1)[CH3:28]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 30163972-Ethoxybenzoyl chlorideHCID 866420471-[4-(4-Ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Product 1

HCID 866605081-(2-Ethoxyphenyl)-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]prop-2-yn-1-one

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature and under an atmosphere of argon, palladium(II) chloride (5.8 mg) and copper(I) iodide were added to a solution of 1-[4-(4-ethynyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (250 mg) and 2-ethoxybenzoyl chloride in tetrahydrofuran. The mixture was stirred at room temperature for 1 minute, and triethylamine (83 mg) was then added. The reaction mixture was stirred at room temperature overnight. 5 g of silica gel were then added, and the solvent was removed under reduced pressure. The residue was purified chromatographically. This gave 1-(2-ethoxyphenyl)-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]prop-2-yn-1-one (244 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. addition5 g of silica gel were then added
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-bfec43cc89fc42e3b3e9486629687409
Source dataset
uspto-grants-2016_06
Patent number
US09357779B2

Reaction notes

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