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

HRID 1893429Notes

Reaction equation

HRID 1893429 reaction equation
[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[N:4][CH:3]=1.CCN(CC1C=CC=CC=1)CC.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[Cl:41][C:42]1[C:50]([C:51]([F:54])([F:53])[F:52])=[CH:49][CH:48]=[CH:47][C:43]=1[C:44](Cl)=[O:45]>ClCCl>[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:44]([C:43]3[CH:47]=[CH:48][CH:49]=[C:50]([C:51]([F:52])([F:53])[F:54])[C:42]=3[Cl:41])=[O:45])[CH2:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 16212021N-benzyl-N-ethylethanamine;1,4-bis(ethenyl)benzene;styreneHCID 654391243-Chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Product 1

HCID 497855433-Chloro-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazineYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (I20) (450 mg, 2.86 mmol) and diethylaminomethyl polystyrene (2855 mg, 9.14 mmol) were slurried in dichloromethane (DCM) (10 mL) and treated with 2-chloro-3-(trifluoromethyl)benzoyl chloride (763 mg, 3.14 mmol). The slurry was stirred at RT for 24 h, whereupon the resin was filtered and washed with dichloromethane (20 mL). The filtrate was concentrated in vacuo to afford 911 mg of material that was purified by flash chromatography (Isolera, 10 g, 0-100% ethyl acetate/iso-hexane) to afford a crude product which was further purified by MDAP to afford desired product in 373 mg.

Workup

  1. filtrationwas filtered
  2. washwashed with dichloromethane (20 mL)
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7eef87896a5845ba9905399646361d67
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

Loading…