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

HRID 1893415Notes

Reaction equation

HRID 1893415 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[Cl:17][C:18]1[C:26]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>ClCCl>[Cl:17][C:18]1[C:26]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([N:7]1[CH2:8][CH2:9][N:4]2[CH:3]=[CH:2][N:1]=[C:5]2[CH2:6]1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 132470465,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine

Product 1

HCID 497850107-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazineYield 49.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine (0.099 g, 0.804 mmol) was suspended in dichloromethane (DCM) (8 ml). Triethylamine (0.123 mL, 0.884 mmol) and 2-chloro-3-(trifluoromethyl)benzoyl chloride (0.195 g, 0.804 mmol) were added and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo, the residue dissolved in 1:1 DMSO/MeOH and purified by mass-directed automated preparative HPLC. Product fractions were concentrated in vacuo to yield an orange gum. This was partitioned between DCM (10 ml) and saturated aqueous sodium bicarbonate (4 ml) and the organic layer separated. This was concentrated in vacuo to yield 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.131 g, 0.397 mmol, 49.4% yield) as a yellow gum.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in 1:1 DMSO/MeOH
  3. custompurified
  4. concentrationProduct fractions were concentrated in vacuo
  5. customto yield an orange gum
  6. customThis was partitioned between DCM (10 ml) and saturated aqueous sodium bicarbonate (4 ml)
  7. customthe organic layer separated
  8. concentrationThis was concentrated in vacuo

Sources & evidence

ORD record
ord-ba8cc65561fc44db92c9427d9238db32
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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