Magnesium orthosilicate → N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-2-(phenylmethyl)benzamide

HRID 976420Notes

Reaction equation

HRID 976420 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([CH2:30][C:31]2[CH:48]=[CH:47][CH:46]=[CH:45][C:32]=2[C:33]([NH:35][C:36]2[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=2)=[O:34])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:40]([C:39]3[CH:38]=[CH:37][C:36]([NH:35][C:33](=[O:34])[C:32]4[CH:45]=[CH:46][CH:47]=[CH:48][C:31]=4[CH2:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:44][CH:43]=3)=[O:41])[CH2:6][C:5]=12

Participants

6

Reactant 4

HCID 66225Magnesium orthosilicateHCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 220996634-[[2-(Phenylmethyl)benzoyl]amino]benzoyl Chloride

Product 1

HCID 18917517N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-2-(phenylmethyl)benzamideYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.75 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.57 g of N,N-diisopropylethylamine in 50 ml of methylene chloride is added 1.53 g of 4-[[2-(phenylmethyl)benzoyl]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 1.97 g of the desired product as an amorphous solid.

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-cab47b35168d40469b92340e7a6c29c6
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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