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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
Notes
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Reaction equation

HRID 356608 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-5a1dc34428f24c12be8cb5a7fc0053cf
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05837704

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes