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

HRID 1739896Notes

Reaction equation

HRID 1739896 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH:5]=[N:4][CH:3]=[CH:2]1.[CH3:12][N:13]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].C(N(CC)CC)C.O1C[CH2:42][CH2:41][CH2:40]1>ClCCl.O>[CH:40]1[CH:41]=[CH:42][N:4]2[CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:1]([C:27]([C:26]3[CH:30]=[CH:31][C:23]([N:13]([CH3:12])[C:14](=[O:22])[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[CH3:21])=[CH:24][CH:25]=3)=[O:28])[CH2:2][C:3]=12

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471Triethylamine2×HCID 1484311H-1,4-BenzodiazepineHCID 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-methylbenzamide

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, 1 N HCl, 1 N 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, 1 N HCl, 1 N 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-3512b9505c274b67bf3e313d514f669b
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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