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

반응식

HRID 1889061 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3368410354f842908d095b3845f43a73
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501946B2

연결된 노트

불러오는 중…