Water → HCID 22099630, compound

HRID 1457698Notes

Reaction equation

HRID 1457698 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:16]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:17]([C:22]([NH:24][C:25]2[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=2)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)C(C)C)(C)C.O>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:29]([C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:22]([C:17]4[C:16]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:23])=[CH:33][CH:32]=3)=[O:30])[CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 110307606,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 114505014-(2-Phenylbenzoylamino)-benzoylchloride

Product 1

HCID 22099630HCID 22099630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.296 g of 6,11-dihydropyrido[2,3-b][1,5]benzodiazepine, 0.604 g of 4-[([1,1'-biphenyl]-2-carbonyl)amino]benzoyl chloride and 0.232 g of N,N-diisopropylethylamine in 6 ml of dichloromethane is stirred at room temperature for 1.5 hours. The mixture is poured into water and extracted with dichloromethane. The extract is washed with H2O, saturated NaHCO3, H2O, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is purified on thick layer silica gel plates with hexane-ethyl acetate (1:2) as solvent to give the product as a solid which is crystallized from ethyl acetate to give off-white crystals, m.p. 220° C.-221° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with H2O, saturated NaHCO3, H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated to dryness
  6. customThe residue is purified on thick layer silica gel plates with hexane-ethyl acetate (1:2) as solvent

Sources & evidence

ORD record
ord-b2719f5e9e164323ab503520af800101
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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