Tetrahydrofuran → N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-N-methyl-2-methylbenzamide

HRID 3563Notes

Reaction equation

HRID 3563 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.[CH3:15][N:16]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].C(N(CC)CC)C.O1CCCC1>ClCCl.O>[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:30]([C:29]3[CH:28]=[CH:27][C:26]([N:16]([CH3:15])[C:17](=[O:25])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])=[CH:34][CH:33]=3)=[O:31])[CH2:6][C:5]=12

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 218370924-(N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride2×

Product 1

HCID 21837046N-[4-(5H-Pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)ylcarbonyl)phenyl]-N-methyl-2-methylbenzamideYield 59.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.27 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0,518 g of 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride, 0.182 g of triethylamine and 7 ml of tetrahydrofuran is stirred at room temperature for 3 hours. To the mixture is added 0.29 g of 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride and 0.10 g of triethylamine in 2 ml of dichloromethane and the mixture stirred for 2 days. The mixture is poured into water and extracted with dichloromethane. The extract is washed with water, 1N HCl, 1N NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is evaporated in vacuo and the residue crystallized from dichloromethane-hexane to give 0.38 g of crystals, m.p. 168°-170° C.

Workup

  1. stirringthe mixture stirred for 2 days
  2. extractionextracted with dichloromethane
  3. washThe extract is washed with water, 1N HCl, 1N NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  6. customThe filtrate is evaporated in vacuo
  7. customthe residue crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-0df072498a024403b3a629783d25ae34
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Reaction notes

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