Ethyl Acetate → HCID 9873768, compound

HRID 441248Notes

Reaction equation

HRID 441248 reaction equation
C(CN1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:39])[C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:38])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)=[CH:19][CH:18]=2)[CH2:8]CC1=O)(O)=O.[CH3:41][N:42]1CC[NH:45][CH2:44][CH2:43]1.[OH:48]N1C2C=CC=CC=2N=N1.Cl.[CH3:59][N:60]([CH3:69])[CH2:61][CH2:62]CN=C=NCC.C([O:73][CH2:74][CH3:75])(=O)C>CN(C)C=O>[CH3:37][C:34]1[CH:33]=[CH:32][C:31]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([C:16]([N:9]3[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:45]([CH2:44][C:43]([N:42]4[CH2:62][CH2:61][N:60]([CH3:59])[CH2:69][CH2:41]4)=[O:48])[C:74](=[O:73])[CH2:75][CH2:8]3)=[O:39])=[CH:22][CH:21]=2)=[O:38])=[CH:36][CH:35]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10530330HCID 10530330, compound

Product 1

HCID 9873768HCID 9873768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-carboxymethyl-5-{4-[2-(4 -methylphenyl)benzoylamino]benzoyl}-1,3,4,5-tetrahydro -1,5-benzodiazepin-2(2H)-one (90 mg), N-methylpiperazine (17 mg) and 1-hydroxybenzotriazole (27 mg) in N,N-dimethylformamide (4 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (39 mg) at ambient temperature and the mixture was stirred at the same temperature for 1.5 hours. The resulting mixture was diluted with ethyl acetate and then the solution was washed with saturated sodium bicarbonate aqueous solution and brine. Drying over magnesium sulfate, filtering and the removal of solvents afforded a crude product. The crude product was triturated with a mixture of diethyl ether and n-hexane (1:1) to give 5-{4-[2-(4-methylphenyl)benzoylamino]benzoyl}-1-[(4-methyl-1-piperazinyl)carbonylmethyl]-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (100 mg) as a white powder.

Workup

  1. washthe solution was washed with saturated sodium bicarbonate aqueous solution and brine
  2. dry with materialDrying over magnesium sulfate
  3. filtrationfiltering
  4. customthe removal of solvents
  5. customafforded a crude product
  6. customThe crude product was triturated with a mixture of diethyl ether and n-hexane (1:1)

Sources & evidence

ORD record
ord-9fdc00e218594749986ba1c887161612
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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