HCID 89690638, compound → HCID 89690555, compound

HRID 1481857Notes

Reaction equation

HRID 1481857 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[CH2:15][CH2:14]2)=[CH:6][C:5]=1[C:26]([F:29])([F:28])[F:27]>C(O)C.O1CCCC1.[Pd]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH3:25])[CH2:15][CH2:14]2)=[CH:6][C:5]=1[C:26]([F:28])([F:29])[F:27]

Participants

5

Reactant 1

HCID 89690638HCID 89690638, compound

Product 1

HCID 89690555HCID 89690555, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-nitro-4-(4-o-tolyl-piperazin-1-yl)-2-trifluoromethyl-benzoic acid methyl ester 9a (212.9 mg, 0.50 mmol, 100 mol %) in ethanol (5.0 ml) and tetrahydrofuran (2.0 ml) was added palladium on carbon (5 wt %) (107.0 mg, 0.05 mmol, 10 mol %) and the reaction was stirred at room temperature for 16 h and then filtered through a pad of Celite. The filtrate was then concentrated to a residue that was purified by column chromatography (dichloromethane to 10% methanol/dichloromethane) to afford 5-amino-4-(4-o-tolyl-piperazin-1-yl)-2-trifluoromethyl-benzoic acid methyl ester 9b (139.5 mg, 0.36 mmol) as an off-white solid. LCMS (ESI) 394 (M+H).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was then concentrated to a residue that
  3. customwas purified by column chromatography (dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-100e962e480f45b0b50267f7de481e7f
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

Loading…