2-Chloro-3-(trifluoromethyl)benzoyl chloride → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-fluorophenyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 1893428Notes

Reaction equation

HRID 1893428 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH2:13][CH2:14][NH:15][CH2:16][C:11]3=[N:10][C:9]=2[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.CCN(CC1C=CC=CC=1)CC.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[Cl:51][C:52]1[C:60]([C:61]([F:64])([F:63])[F:62])=[CH:59][CH:58]=[CH:57][C:53]=1[C:54](Cl)=[O:55]>ClCCl>[Cl:51][C:52]1[C:60]([C:61]([F:63])([F:64])[F:62])=[CH:59][CH:58]=[CH:57][C:53]=1[C:54]([N:15]1[CH2:14][CH2:13][N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[C:9]([C:17]([F:18])([F:19])[F:20])[N:10]=[C:11]2[CH2:16]1)=[O:55]

Participants

5

Reactant 3

HCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 16212021N-benzyl-N-ethylethanamine;1,4-bis(ethenyl)benzene;styreneHCID 665993343-(4-Fluorophenyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Product 1

HCID 497854577-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-fluorophenyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Fluorophenyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (I14) (285 mg, 1 mmol) and diethylaminomethyl polystyrene (1000 mg, 3.20 mmol) were slurried in dichloromethane (DCM) (10 mL) and treated with 2-chloro-3-(trifluoromethyl)benzoyl chloride (267 mg, 1.100 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 in 428 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 in 428 mg

Sources & evidence

ORD record
ord-c44e8e3ac6584947924d1feb12b8139d
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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