5-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridine-3-sulfonic acid (2-cyclopropylethyl)amide

HRID 1820630Notes

Reaction equation

HRID 1820630 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:35])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[C:31]([F:34])([F:33])[F:32])[CH2:19][CH2:18]3)=[C:14](Br)[CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][CH2:5][NH:6][S:7]([C:10]2[CH:11]=[N:12][C:13]([N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:35])[C:24]4[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=4[C:31]([F:34])([F:32])[F:33])[CH2:19][CH2:18]3)=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 112961565-Bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide

Product 1

HCID 113640636-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridine-3-sulfonic acid (2-cyclopropylethyl)amideYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 5-bromo-6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]-pyridine-3-sulfonic acid (2-cyclopropylethyl)amide (0.100 g, 0.173 mmol) in methanol (5.0 mL) was added Pd/C (0.050 g,12 mol %). The mixture was placed under an atmosphere of hydrogen for 24 hours. The reaction mixture was filtered through celite and concentrated in vacuo. The crude product was purified by column chromatography, eluting with a solvent gradient of 35% ethyl acetate and 65% hexane to yield the desired product (0.020 9, 24%). 1H NMR (300 MHz, CDCl3) δ 8.58-8.57, 7.87-7.83, 7.76-7.71, 7.26-7.23, 7.08-7.04, 6.65-6.62, 4.60-4.56, 4.00-3.93, 3.86-3.64, 3.32-3.28, 3.04-2.97,1.40-1.33, 0.59-0.53, 0.43-0.37, 0.025-0.008. 13C NMR (75 MHz, CDCl3) δ 166.1, 162.6, 159.7, 148.2, 136.7, 129.7, 125.1, 124.7, 116.8, 116.5, 114.9, 114.7, 105.8, 46.5, 44.3, 44.2, 43.4, 41.4, 34.4, 8.2, 4.2. MS (ES+) m/z 501 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography
  4. washeluting with a solvent gradient of 35% ethyl acetate and 65% hexane

Sources & evidence

ORD record
ord-2ac3a066d21c44cab7c0094e352806ad
Source dataset
uspto-grants-2009_10
Patent number
US07605161B2

Reaction notes

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