2-Amino-p-cymene → HCID 71238849, 화합물

HRID 80830노트

반응식

HRID 80830 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:17]=[C:16]([O:18][CH3:19])[C:12]([C:13]([O-])=[O:14])=[C:11]([CH:20]=[CH2:21])[N:10]=1.[CH:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:32])=[C:29]([CH:31]=1)[NH2:30])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:17]=[C:16]([O:18][CH3:19])[C:12]2[C:13](=[O:14])[N:30]([C:29]3[CH:31]=[C:25]([CH:22]([CH3:23])[CH3:24])[CH:26]=[CH:27][C:28]=3[CH3:32])[CH2:21][CH2:20][C:11]=2[N:10]=1

참가 물질

5

반응물 2

HCID 1374142-Amino-p-cymeneHCID 866902806-(2,6-Dimethylphenyl)-4-methoxy-2-vinylnicotinate

생성물 1

HCID 71238849HCID 71238849, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

A solution of 6-(2,6-dimethylphenyl)-4-methoxy-2-vinylnicotinate (1.77 g, 5.95 mmol) and 5-isopropyl-2-methylaniline (4.44 g, 29.8 mmol) in toluene (26.5 mL) and acetic acid (13.2 mL) was heated to 110° C. and stirred at that temperature. After 12 h, the reaction mixture was removed from the heat and concentrated on the rotovap to remove the bulk of the solvent. The residue was partitioned between EtOAc and aqueous 1 N sodium hydroxide solution with added brine. The layers were separated and the aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, then dried over sodium sulfate, filtered, and concentrated. The residue was purified by FCC (0-15% EtOAc/DCM) to provide 2-(2,6-dimethylphenyl)-6-(5-isopropyl-2-methylphenyl)-4-methoxy-7,8-dihydro-1,6-naphthyridin-5(6H)-one. The product contained some 5-isopropyl-2-methylaniline and was used in the next step without further purification. MS (ESI+) m/z 415.2 (M+H)+.

후처리

  1. customthe reaction mixture was removed from the
  2. temperatureheat
  3. concentrationconcentrated on the rotovap
  4. customto remove the bulk of the solvent
  5. customThe residue was partitioned between EtOAc and aqueous 1 N sodium hydroxide solution with added brine
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with EtOAc (3×)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by FCC (0-15% EtOAc/DCM)

출처 및 근거

ORD 기록
ord-843bf64278b74feb9a10db6d0def6ae9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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