Sodium hydride → [2-[(3-Amino-2-pyridinyl)[3-(dimethylamino)propyl]amino]phenyl]phenylmethanone

HRID 637452

Reaction equation

HRID 637452 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[N:6][CH:7]=[CH:8][CH:9]=1.Cl.[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30]Cl>CN(C)C=O>[CH3:26][N:27]([CH3:32])[CH2:28][CH2:29][CH2:30][N:10]([C:5]1[C:4]([NH2:3])=[CH:9][CH:8]=[CH:7][N:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 15586652{2-[(3-Aminopyridin-2-yl)amino]phenyl}(phenyl)methanone

Product 1

HCID 53769600[2-[(3-Amino-2-pyridinyl)[3-(dimethylamino)propyl]amino]phenyl]phenylmethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (in mineral oil) in anhydrous dimethylformamide, under nitrogen atmosphere was added, portionwise, [2-[(3-amino-2-pyridinyl)amino]phenyl]phenylmethanone. To the mixture was added 3-dimethylaminopropyl chloride hydrochloride to give a solution containing some of the title compound as indicated by chemical ionization mass spectrascopy analysis. With time, this cyclized spontaneously to the corresponding pyrido[2,3-b][1,4]benzodiazepine.

Workup

  1. additionunder nitrogen atmosphere was added
  2. customto give a solution

Sources & evidence

ORD record
ord-e7f9b374fc8246d68d481efb2cbb93bb
Source dataset
uspto-grants-1985_12
Patent number
US04556667

Linked notes

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