Triethylamine → HCID 22099746, compound

HRID 1457679Notes

Reaction equation

HRID 1457679 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[NH:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:23][C:24]1[O:25][CH:26]=[CH:27][C:28]=1[C:29]([NH:31][C:32]1[N:37]=[CH:36][C:35]([C:38](Cl)=[O:39])=[CH:34][CH:33]=1)=[O:30]>ClCCl>[N:1]1[C:6]2[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[N:10]([C:38]([C:35]3[CH:34]=[CH:33][C:32]([NH:31][C:29]([C:28]4[CH:27]=[CH:26][O:25][C:24]=4[CH3:23])=[O:30])=[N:37][CH:36]=3)=[O:39])[CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 22099840HCID 22099840, compound

Product 1

HCID 22099746HCID 22099746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 0.296 g of 6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine and 624 μL of triethylamine in 3 ml of dichloromethane is added a solution of 6-[(2-methyl-3-furanylcarbonyl)amino]-3-pyridinecarbonyl chloride in 4 ml of dichloromethane. The mixture is stirred at room temperature for 16 hours and the solvent removed under vacuum. To the residue is added 1M NaHCO3 and the mixture extracted with ethyl acetate. The extract is washed with H2O, 1M NaHCO3 brine and dried (Na2SO4). The solvent is removed under vacuum and the residue chromatographed on silica gel with ethyl acetate-hexane as solvent to give the product as a solid.

Workup

  1. customthe solvent removed under vacuum
  2. additionTo the residue is added 1M NaHCO3
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe extract is washed with H2O, 1M NaHCO3 brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is removed under vacuum
  7. customthe residue chromatographed on silica gel with ethyl acetate-hexane as solvent

Sources & evidence

ORD record
ord-e4af2b813aca4c4e8ecb985e1f7cb22e
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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