Water → 2,2-Dimethyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyrazinyl]phenyl]propanamide

HRID 1780589Notes

Reaction equation

HRID 1780589 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[N:4][CH:3]=1.[F:22][C:23]([F:28])([F:27])C([O-])=O.[Na+].C(OCC)C.O>CN1CCCC1=O>[CH3:18][C:17]([CH3:20])([CH3:19])[C:16]([NH:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:23]([F:28])([F:27])[F:22])[N:7]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 517019Sodium TrifluoroacetateHCID 19047047N-[2-(6-Bromo-2-pyrazinyl)-4-methylphenyl]-2,2-dimethyl-propanamide

Product 1

HCID 190470512,2-Dimethyl-N-[4-methyl-2-[6-(trifluoromethyl)-2-pyrazinyl]phenyl]propanamideYield 18%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product obtained from Step B (0.8 g, 2.3 mmol) was dissolved in N-methylpyrrolidinone (16 mL). Cuprous iodide (1.7 g, 9.2 mmol) and sodium trifluoroacetate (2.5 g, 18.4 mmol) were then added and the resultant mixture heated at 180° C. for 6 h. After cooling to room temperature, diethyl ether (200 mL) and water (100 mL) were added. The two-phase mixture was filtered through a pad of Celite and the filter cake subsequently washed with three 50 mL-portions of ether. The layers of the filtrate were separated and the ether layer dried (MgSO4). The ethereal solution was evaporated and the residue chromatographed on silica gel eluting with 15% ethyl acetate/hexane. In this manner, 0.14 g (18%) of the title compound was obtained as a yellow semisolid. 1H NMR (300 MHz,CDCl3) δ 10.25 (br s,1H), 9.18 (s,1H), 8.93 (s,1H), 8.33-8.35 (m,1H), 7.41 (s, 1H), 7.33-7.35 (m,1H), 2.41 (s,3H), 1.25 (s,9H). 19F NMR (282 MHz, CDCl3) δ 67.2.

Workup

  1. filtrationThe two-phase mixture was filtered through a pad of Celite
  2. washthe filter cake subsequently washed with three 50 mL-portions of ether
  3. customThe layers of the filtrate were separated
  4. dry with materialthe ether layer dried (MgSO4)
  5. customThe ethereal solution was evaporated
  6. customthe residue chromatographed on silica gel eluting with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2cc63510589d41b980ba5ee93a246333
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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