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

HRID 984843ノート

反応式

HRID 984843 の反応式
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

参加物

4

反応物 2

HCID 6212ChloroformHCID 225089424-Chloro-1,8-dimethyl-imidazo[1,2-A]quinoxaline2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 3301Ethylenediamine溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-af9636153a5740eab03ffebc23f5d2ac
出典データセット
uspto-grants-2005_03
特許番号
US06869956B2

反応ノート

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