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Potassium Acetate → 5,11-Dihydro-5-ethyl-11-methyl-2-(2-pyrrolyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 356608
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인쇄 미리보기

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HRID 356608 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:19][CH3:20])[C:7](=[O:18])[C:8]3[CH:17]=[CH:16][CH:15]=[N:14][C:9]=3[N:10]([CH3:13])[C:11]=2[N:12]=1.C(OC([C:28]1[NH:29][CH:30]=[CH:31][CH:32]=1)=O)(C)(C)C.C([O-])(=O)C.[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN1CCCC1=O>[CH2:19]([N:6]1[C:7](=[O:18])[C:8]2[CH:17]=[CH:16][CH:15]=[N:14][C:9]=2[N:10]([CH3:13])[C:11]2[N:12]=[C:2]([C:28]3[NH:29][CH:30]=[CH:31][CH:32]=3)[CH:3]=[CH:4][C:5]1=2)[CH3:20]
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참가 물질

6

반응물 3

HCID 517044Potassium AcetateHCID 15458947tert-butyl 1H-pyrrole-2-carboxylateHCID 189388852-chloro-5,11-dihydro-5-ethyl-11-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

생성물 1

HCID 159562955,11-Dihydro-5-ethyl-11-methyl-2-(2-pyrrolyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
140 °C

실험 절차

A mixture of 2-chloro-5,11-dihydro-5-ethyl-11-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.21 g), (t-butoxycarbonyl)pyrrole (0.25 g), potassium acetate (0.20 g), Pd(PPh3)2Cl2 (0.030 g), and 1-methyl-2-pyrrolidinone (2.5 mL) were heated in a sealed tube at 140° C. for 14 h. After removing the solvent, water was added and the product was extracted with CH2Cl2, dried (anhyd Na2 SO4), filtered, and evaporated. The residue was chromatographed over silica gel (ethyl acetate/methylene chloride, 1:9) and was further purified by preparative plate chromatography (ethyl acetate/methylene chloride, 1:9) to give, after recrystallization from ethyl acetate/hexanes, 0.020 g of the title compound, mp 161°-162° C.

후처리

  1. customAfter removing the solvent, water
  2. additionwas added
  3. extractionthe product was extracted with CH2Cl2
  4. customdried (anhyd Na2 SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed over silica gel (ethyl acetate/methylene chloride, 1:9)
  8. customwas further purified by preparative plate chromatography (ethyl acetate/methylene chloride, 1:9)
  9. customto give
  10. customafter recrystallization from ethyl acetate/hexanes, 0.020 g of the title compound, mp 161°-162° C.

출처 및 근거

ORD 기록
ord-5a1dc34428f24c12be8cb5a7fc0053cf
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05837704

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