1-(6-Fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid → 8-Carbobenzoxy-2-fluoro-7,8,9,10-tetrahydro5H-pyrazino[1,2-a]pyrido[3,2-e]pyrazin-6(6aH)-one

HRID 1390353노트

반응식

HRID 1390353 반응식
[F:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH:9]2[C:24]([OH:26])=O)[C:5]([N+:27]([O-])=O)=[CH:4][CH:3]=1>[Fe].C(O)(=O)C>[C:14]([N:11]1[CH2:12][CH2:13][N:8]2[C:6]3[N:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[NH:27][C:24](=[O:26])[CH:9]2[CH2:10]1)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

참가 물질

4

반응물 1

HCID 233397701-(6-Fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid

생성물 1

HCID 233397608-Carbobenzoxy-2-fluoro-7,8,9,10-tetrahydro5H-pyrazino[1,2-a]pyrido[3,2-e]pyrazin-6(6aH)-one

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

To a solution of 14.0 g. of 1-(6-fluoro-3-nitro-2-pyridinyl)-4-carbobenzoxypiperazine-2-carboxylic acid in 300 ml. of acetic acid is added, while stirring, 7.0 g. of iron powder. The mixture is warmed to 55° for 3 hours then concentrated. The residue is treated with water and extracted with methylene chloride, dried (MgSO4) and concentrated. The residue is placed on a dry column of alumina and eluted with chloroform. The product band in the column is cut out and the product is washed from the alumina with methanol. Concentration of the methanol wash gives 5.0 g. of the light green-colored title product. Recrystallization from ethanol gives 2.2 g. of pure product, m.p. 210°-214°.

후처리

  1. temperatureThe mixture is warmed to 55° for 3 hours
  2. concentrationthen concentrated
  3. additionThe residue is treated with water
  4. extractionextracted with methylene chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washeluted with chloroform
  8. washthe product is washed from the alumina with methanol
  9. washConcentration of the methanol wash
  10. customgives 5.0 g

출처 및 근거

ORD 기록
ord-866fe73220584e7f8b5edee7eda2f921
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04138564

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