Ethyl Acetate → HCID 22011022, compound

HRID 323152Notes

Reaction equation

HRID 323152 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:37]=[CH:36][C:20]([C:21]([N:23](C)[C:24]4C=CC=CC=4OCC(O)=O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.[OH2:45].ON1[C:51]2[CH:52]=CC=[CH:55][C:50]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:68]([O:71][CH2:72][CH3:73])(=O)[CH3:69]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:24])[C:69]4[CH:52]=[CH:51][CH:50]=[CH:55][C:68]=4[O:71][CH2:72][C:73]([N:42]4[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]4)=[O:45])=[O:22])=[CH:36][CH:37]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22010657HCID 22010657, compound

Product 1

HCID 22011022HCID 22011022, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-(2-carboxymethoxyphenyl)benzamide (295 mg), N-methylpiperazine (60 mg) and 1-hydroxybenzotriazole hydrate (97 mg) in N,N-dimethylformamide (5 ml) was added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (137 mg) at 0° C. and the mixture was stirred at ambient temperature for 15 hours. The resulting mixture was diluted with ethyl acetate and then the organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying, filtering and removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (eluent; 3% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(4-methyl-1-piperazinyl)carbonylmethoxyphenyl]benzamide (213 mg) as a white powder.

Workup

  1. washthe organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine
  2. customDrying
  3. filtrationfiltering
  4. customremoval of solvents
  5. customafforded a crude product
  6. customThe crude product was chromatographed on silica gel (eluent; 3% methanol in chloroform)

Sources & evidence

ORD record
ord-e188c02547534ae6af47848c73dedf8f
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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