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

HRID 1893417Notes

Reaction equation

HRID 1893417 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:4]=[C:5]2[CH2:10][NH:9][CH2:8][CH2:7][N:6]2[CH:11]=1.CCN(CC1C=CC=CC=1)CC.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[Cl:44][C:45]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:46]=1[C:47](Cl)=[O:48]>ClCCl>[Cl:44][C:45]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:46]=1[C:47]([N:9]1[CH2:8][CH2:7][N:6]2[CH:11]=[C:3]([C:2]([F:12])([F:1])[F:13])[N:4]=[C:5]2[CH2:10]1)=[O:48]

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 147199282-(trifluoromethyl)-5H,6H,7H,8H-imidazo[1,2-a]pyrazine2×HCID 16212021N-benzyl-N-ethylethanamine;1,4-bis(ethenyl)benzene;styrene

Product 1

HCID 497850127-[(2,4-Dichlorophenyl)carbonyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.096 g, 0.5 mmol, intermediate 4) and diethylaminomethyl polystyrene (0.469 g, 1.500 mmol) were slurried in dichloromethane (DCM) (5 ml). 2,4-Dichlorobenzoyl chloride (0.084 ml, 0.600 mmol) was added and the mixture stirred at room temperature for 24 h. The resin was filtered, washed with dichloromethane and the filtrate concentrated in vacuo to afford crude product which was purified by flash chromatography (Biotage SP4, 25+S, eluting with a 0-100% gradient of ethyl acetate/iso-hexane) to afford 7-[(2,4-dichlorophenyl)carbonyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (0.178 g, 0.489 mmol, 98% yield).

Workup

  1. filtrationThe resin was filtered
  2. washwashed with dichloromethane
  3. concentrationthe filtrate concentrated in vacuo
  4. customto afford crude product which
  5. customwas purified by flash chromatography (Biotage SP4, 25+S
  6. washeluting with a 0-100% gradient of ethyl acetate/iso-hexane)

Sources & evidence

ORD record
ord-ad4332c500ef4cbe8e315c3566f619e3
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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