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

HRID 1459552Notes

Reaction equation

HRID 1459552 reaction equation
[H-].[Na+].[CH:3]1[CH:4]=[CH:5][N:6]2[CH2:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=4[Cl:34])=[CH:21][CH:20]=3)=[O:18])[CH2:8][C:7]=12.[I-].C[CH:38]=[N+:39]=[CH:40]C.O1CCC[CH2:43]1>C(OCC)C>[CH3:38][N:39]([CH2:40][N:25]([C:22]1[CH:21]=[CH:20][C:19]([C:17]([N:9]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[CH2:12][N:6]3[CH:5]=[CH:4][CH:3]=[C:7]3[CH2:8]2)=[O:18])=[CH:24][CH:23]=1)[C:26](=[O:35])[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34])[CH3:43]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 9826254N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)-phenyl]2,4-dichlorobenzamideHCID 21892197N,N-dimethylmethyleneammoniumiodide

Product 1

HCID 70057901N-[(Dimethylamino)methyl]-N-(4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2,4-dichlorobenzamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension under argon of 0.072 g of sodium hydride (60% in oil) in 10 ml of tetrahydrofuran is added 0.71 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2,4-dichlorobenzamide and the mixture stirred at room temperature for 1 hour. To the mixture is added N,N-dimethylmethylene-ammonium iodide and the mixture stirred 20 hours. The mixture is diluted with diethyl ether (30 ml), filtered and the filtrate concentrated under vacuum. The residue is triturated with hexane to give 0.76 g of white solid, m.p. 126°-129° C.

Workup

  1. stirringthe mixture stirred 20 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue is triturated with hexane

Sources & evidence

ORD record
ord-885124b7bd464fcca8a891436f0a3221
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

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