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

HRID 1893430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893430
[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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a4cc7ddd9db34649b589a2e2842584db
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513248B2

Notizen zur Reaktion

Wird geladen…