Magnesium orthosilicate → Biphenyl-2-carboxylic acid [4-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-phenyl]-amide

HRID 1940810Notes

Reaction equation

HRID 1940810 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)C(C)C)(C)C.[C:24]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:25]([C:30]([NH:32][C:33]2[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=2)=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1.[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(Cl)Cl>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:37]([C:36]3[CH:35]=[CH:34][C:33]([NH:32][C:30]([C:25]4[C:24]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:31])=[CH:41][CH:40]=3)=[O:38])[CH2:6][C:5]=12

Participants

6

Reactant 4

HCID 66225Magnesium orthosilicateHCID 81531DiisopropylethylamineHCID 114505014-(2-phenylbenzoylamino)-benzoylchlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 9935001Biphenyl-2-carboxylic acid [4-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-phenyl]-amideYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.65 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.52 g of N,N-diisopropylethylamine in 25 ml of methylene chloride is added 1.34 g of 4-[([1,1'-biphenyl]-2-carbonyl)amino]benzoyl chloride followed by stirring at room temperature for 18 hours. The reaction mixture is washed with water and saturated aqueous NaHCO3 and the organic layer dried (Na2SO4). The organic layer is passed through hydrous magnesium silicate and the filtrate concentrated in vacuo to give a residue which is dissolved in methylene chloride and passed through hydrous magnesium silicate two additional times to give upon concentration in vacuo to give 1.02 g of the desired product as a residue. M+ =482.

Workup

  1. washThe reaction mixture is washed with water and saturated aqueous NaHCO3
  2. dry with materialthe organic layer dried (Na2SO4)
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a residue which
  5. customto give upon concentration in vacuo

Sources & evidence

ORD record
ord-35c39143f38442509ea4cbb394a904a9
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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