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

HRID 1889061

反応式

HRID 1889061 の反応式
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[N:4][N:3]=1.BrC1N2CCN(C(OC(C)(C)C)=O)CC2=NN=1.CCN(CC1C=CC=CC=1)CC.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[Cl:58][C:59]1[C:67]([C:68]([F:71])([F:70])[F:69])=[CH:66][CH:65]=[CH:64][C:60]=1[C:61](Cl)=[O:62]>ClCCl>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:61]([C:60]3[CH:64]=[CH:65][CH:66]=[C:67]([C:68]([F:69])([F:70])[F:71])[C:59]=3[Cl:58])=[O:62])[CH2:10][C:5]2=[N:4][N:3]=1

参加物

6

反応物 4

HCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 16212021N-benzyl-N-ethylethanamine;1,4-bis(ethenyl)benzene;styreneHCID 179987223-Bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazineHCID 17998723tert-Butyl 3-bromo-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate

生成物 1

HCID 665992213-Bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-Bromo-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (prepared by standard BOC deprotection of tert-Butyl 3-bromo-5,6-dihydro-1,2,4-triazolo[4,3-a]pyrazine-7(8H)-carboxylate, CAS [723286-80-4], commercially available e.g. from Allichem, Ark Pharm or Bepharm) (0.6 mmol) and diethylaminomethyl polystyrene (0.6 g, 1.92 mmol) were slurried in Dichloromethane (DCM) (7 mL) under argon. 2-Chloro-3-(trifluoromethyl)benzoyl chloride (0.16 g, 0.66 mmol, commercially available e.g. from Apollo Scientific or Shanghai FWD Chemicals) was added to the reaction. The mixture was stirred for 4 hours. The resin was filtered, washed with Dichloromethane (50 mL) and concentrated in vacuo to afford crude product. The crude product was purified by using mass-directed automated (preparative) HPLC (MDAP). The fractions containing the products were evaporated, diluted with diethyl ether and treated with 1 mL of HCl in diethyl ether; the solutions were stirred for 30 min. and solvent evaporated to give 3-bromo-7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.268 g). LC/MS [M+H]+=410.9, retention time=2.07 minutes (5 minute method).

後処理

  1. filtrationThe resin was filtered
  2. washwashed with Dichloromethane (50 mL)
  3. concentrationconcentrated in vacuo
  4. customto afford crude product
  5. customThe crude product was purified
  6. additionThe fractions containing the products
  7. customwere evaporated
  8. additiondiluted with diethyl ether
  9. additiontreated with 1 mL of HCl in diethyl ether
  10. stirringthe solutions were stirred for 30 min.
  11. customsolvent evaporated

出典と根拠

ORDレコード
ord-3368410354f842908d095b3845f43a73
出典データセット
uspto-grants-2013_08
特許番号
US08501946B2

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