Potassium Carbonate → HCID 131719419, compound

HRID 441262Notes

Reaction equation

HRID 441262 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[NH:32][C:33](=[O:47])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)[C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)=[O:20])[C:10](=O)[CH2:9][CH2:8]1)=[O:6].Cl.[CH3:49][N:50]([CH3:55])[CH2:51][CH2:52][CH2:53]Cl.C(=O)([O-])[O-:57].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:49][N:50]([CH3:55])[CH2:51][CH2:52][CH2:53][O:57][C:29]1[CH:30]=[C:31]([NH:32][C:33](=[O:47])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)[CH:2]=[CH:3][C:4]=1[C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]([N:21]2[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]2)=[O:20])[CH2:10][CH2:9][CH2:8]1)=[O:6]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 22405089HCID 22405089, compound

Product 1

HCID 131719419HCID 131719419, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-{3-hydroxy-4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[(4-methyl-1-piperazinyl)carbonylmethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (350 mg), 3-dimethylaminopropyl chloride hydrochloride (96.4 mg) and potassium carbonate (230 mg) in N,N-dimethylformamide (15 ml) were stirred for 4 hours at 80° C. The mixture was diluted with ethyl acetate and washed with water, saturated aqueous sodium bicarbonate and brine. The organic solution was dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (SiO2 10 g, 15% methanol in chloroform) to give 5-{3-dimethylaminopropoxy-4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[(4-methyl-1-piperazinyl)carbonylmethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin -(2H)-one (150 mg).

Workup

  1. washwashed with water, saturated aqueous sodium bicarbonate and brine
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (SiO2 10 g, 15% methanol in chloroform)

Sources & evidence

ORD record
ord-2d5853ffc70b4965be59f3add6de592d
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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