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

HRID 55220Notes

Reaction equation

HRID 55220 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-dimethylmethyleneammonium 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-b660e488ec7c4e9a839a3379252b7abd
Source dataset
uspto-grants-1997_04
Patent number
US05624923

Reaction notes

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