O-Phenylenediamine → HCID 70114277、化合物

HRID 868945ノート

反応式

HRID 868945 の反応式
[CH3:1][C:2]1[C:3]([CH2:12][CH2:13][C:14](O)=O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17]1([NH2:24])[C:18]([NH2:23])=[CH:19][CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1>[NH:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:24]=[C:14]1[CH2:13][CH2:12][C:3]1[C:2]([CH3:1])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

参加物

6

反応物 3

HCID 7243O-PhenylenediamineHCID 10340Sodium CarbonateHCID 2581413-(3-Methylquinoxalin-2-yl)propanoic acid

生成物 1

HCID 70114277HCID 70114277、化合物収率 6.2%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

3-(3-Methylquinoxalin-2-yl)propanoic acid (98 mg, 0.45 mmol) and benzene-1,2-diamine (98 mg, 0.45 mmol) were suspended in 4 M HCl in 1,4-dioxane (6 mL) and heated in the microwave (150° C., 2.5 h). The crude reaction was poured into saturated aqueous Na2CO3 solution (30 mL) and extracted with EtOAc (3×50 mL). The organic layers were combined, washed with brine (1×50 mL), dried (Na2SO4), filtered and concentrated. The crude material was purified by RPLC (Gilson). Fractions containing the compound were combined, diluted with EtOAc and washed with saturated aqueous Na2CO3, dried (Na2SO4), filtered and concentrated to give 2-(2-(1H-benzo[d]imidazol-2-yl)ethyl)-3-methylquinoxaline (8 mg) as an orange oil. LC-MS m/z 289 (M+H+).

後処理

  1. customThe crude reaction
  2. extractionextracted with EtOAc (3×50 mL)
  3. washwashed with brine (1×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by RPLC (Gilson)
  8. additionFractions containing the compound
  9. additiondiluted with EtOAc
  10. washwashed with saturated aqueous Na2CO3
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-e1aad603e8d64a6d9d08400beb469181
出典データセット
uspto-grants-2015_03
特許番号
US08969349B2

反応ノート

読み込み中…