Methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate → methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate

HRID 715987노트

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HRID 715987 반응식
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([NH:5][C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([N+:16]([O-])=O)[C:9]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=O)=[CH:8][CH:7]=1)=[O:4]>C(O)(=O)C.[Fe]>[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([NH:5][C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[N:16]=[C:20]3[CH2:21][CH2:22][CH2:23][N:19]3[C:9]2=[CH:8][CH:7]=1)=[O:4]

참가 물질

4

반응물 1

HCID 70982623Methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate2회

생성물 1

HCID 70983330methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate수율 79.7%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

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온도
115 °C

실험 절차

A mixture of methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate (Intermediate 57, 0.89 g), and iron powder (1.37 g) in acetic acid (25 mL) was stirred and heated at 115° C. for 2.5 hours. After cooling, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and 2M sodium hydroxide solution and filtered through celite. The organic phase was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 50-100%. The product was repurified by chromatography on silica, eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10% to give methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (0.616 g) as an off-white solid.

후처리

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. filtration2M sodium hydroxide solution and filtered through celite
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 50-100%
  10. customThe product was repurified by chromatography on silica
  11. washeluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%

출처 및 근거

ORD 기록
ord-e2d4b102ca7d4390bc7dcbfc2dac7315
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187494B2

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