O-Phenylenediamine → HCID 70114277, 화합물

HRID 868945노트

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HRID 868945 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 70114277HCID 70114277, 화합물수율 6.2%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 312751,4-Dioxane용매

반응 조건

온도
150 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-e1aad603e8d64a6d9d08400beb469181
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969349B2

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