Triethylamine → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 1893416Notes

Reaction equation

HRID 1893416 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:4]=[C:5]2[CH2:10][NH:9][CH2:8][CH2:7][N:6]2[CH:11]=1.C(N(CC)CC)C.[Cl:21][C:22]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>ClCCl>[Cl:21][C:22]1[C:30]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([N:9]1[CH2:8][CH2:7][N:6]2[CH:11]=[C:3]([C:2]([F:12])([F:1])[F:13])[N:4]=[C:5]2[CH2:10]1)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 147199282-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,2-a]pyrazine2×

Product 1

HCID 497850117-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazineYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (1.06 g, 5.55 mmol, Intermediate 4) and triethylamine (0.850 ml, 6.10 mmol) were dissolved in dichloromethane (DCM) (25 ml). 2-chloro-3-(trifluoromethyl)benzoyl chloride (1.348 g, 5.55 mmol) was added and the mixture stirred at room temperature for 24 h. The solvents were removed in vacuo and the solid partitioned between dichloromethane (100 ml) and saturated sodium bicarbonate solution (50 ml). The aqueous phase was extracted with dichloromethane (3×50 ml), the combine organic extracts were dried over anhydrous sodium sulfate and then concentrated to afford 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (2.22 g, 5.58 mmol, 101% yield).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe solid partitioned between dichloromethane (100 ml) and saturated sodium bicarbonate solution (50 ml)
  3. extractionThe aqueous phase was extracted with dichloromethane (3×50 ml)
  4. dry with materialthe combine organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4222bd017e5d4f5ab91a8b9b8277e41b
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

Loading…