Chloroform → 4(2'-Aminoethyl)amino-1,8-dimethylimidazo(1,2-a)quinoxaline

HRID 984843노트

반응식

HRID 984843 반응식
Cl[C:2]1[C:3]2[N:4]([C:13]([CH3:16])=[CH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([CH3:12])[CH:6]=2.C(Cl)(Cl)Cl>C(N)CN>[NH2:4][CH2:3][CH2:2][NH:11][C:2]1[C:3]2[N:4]([C:13]([CH3:16])=[CH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([CH3:12])[CH:6]=2

참가 물질

4

반응물 2

HCID 6212ChloroformHCID 225089424-Chloro-1,8-dimethyl-imidazo[1,2-A]quinoxaline2회

생성물 1

HCID 98137584(2'-Aminoethyl)amino-1,8-dimethylimidazo(1,2-a)quinoxaline수율 174.2%

시약·촉매·용매 1

HCID 3301Ethylenediamine용매

실험 절차

A solution of 4-chloro-1,8-dimethylimidazo(1,2-a)quinoxaline (compound 5) (4.8 g, 21 mmol) in ethylenediamine (300 mL) was heated at 60° C. under nitrogen gas (N2) for 16 hours. The solvent was evaporated under vacuum. The residue was diluted with EtOAc (200 mL), washed with saturated Na2CO3 and brine, dried over MgSO4, filtered and concentrated. Flash chromatography using methanol (MeOH) provided a solid, which was then dissolved with CHCl3 and filtered to remove any dissolved silica gel. The filtrate was concentrated under vacuum, providing the title compound 6 as a white solid (4.67 g). 1H NMR (500 MHz, CDCl3) δ 7.88 (s, 1H), 7.63 (d, J=8.3 Hz, 1H), 7.26 (s, 1H), 7.22 (d, J=8.3 Hz, 1H), 6.31 (s, 1H), 3.63 (apparent q, J=5.9 Hz, 2H), 2.96 (t, J=6.0 Hz, 2H), 2.88 (s, 3H), 1.38 (br, 2H); MS (ESI), m/z 256.15 [(M+H)+; calculated for compound 6, C14H17N5:255.15].

후처리

  1. customThe solvent was evaporated under vacuum
  2. additionThe residue was diluted with EtOAc (200 mL)
  3. washwashed with saturated Na2CO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customprovided a solid, which
  8. filtrationfiltered
  9. customto remove any dissolved silica gel
  10. concentrationThe filtrate was concentrated under vacuum

출처 및 근거

ORD 기록
ord-af9636153a5740eab03ffebc23f5d2ac
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869956B2

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