2,4-Dichlorobenzoyl chloride → 3-Chloro-7-[(2,4-dichlorophenyl)carbonyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 1893430Notes

Reaction equation

HRID 1893430 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[CH:50]=[C:49]([Cl:51])[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][C:49]([Cl:51])=[CH:50][C:42]=3[Cl:41])=[O:45])[CH2:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl 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 497855443-Chloro-7-[(2,4-dichlorophenyl)carbonyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

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 2,4-dichlorobenzoyl chloride (0.439 mL, 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 crude product. The product was purified by flash chromatography (Isolera, 10 g, 0-100% ethyl acetate/iso-hexane) to afford product then by MDAP (High pH method) to afford clean desired product in 350 mg.

Workup

  1. filtrationwas filtered
  2. washwashed with dichloromethane (20 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford crude product
  5. customThe product was purified by flash chromatography (Isolera, 10 g, 0-100% ethyl acetate/iso-hexane)
  6. customto afford product

Sources & evidence

ORD record
ord-a4cc7ddd9db34649b589a2e2842584db
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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