1,1'-Carbonyldiimidazole → 3-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester

HRID 449741Notes

Reaction equation

HRID 449741 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][N:6]([C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[C:16]([NH2:22])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:25]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][CH2:34][C:35](O)=[O:36])=[CH:29][CH:28]=1)#[N:26].C1N=CN(C(N2C=NC=C2)=O)C=1>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH2:5][N:6]([C:13](=[O:23])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[C:16]([NH:22][C:35](=[O:36])[CH2:34][NH:33][C:30]2[CH:31]=[CH:32][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)[CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 817965N-(4-Cyanophenyl)glycineHCID 184123363-[(3-Amino-4-methylamino-benzoyl)-phenyl-amino]propionic acid methyl ester

Product 1

HCID 667063283-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of 1b (23.2 mmol) and N-(4-cyano-phenyl)-glycine (23.2 mmol) were coupled with CDI (23.2 mmol) in dry THF at room temperature. After completion of the reaction the mixture was evaporated to dryness and the crude product was used without further purification.

Workup

  1. customAfter completion of the reaction the mixture
  2. customwas evaporated to dryness
  3. customthe crude product was used without further purification

Sources & evidence

ORD record
ord-f6f5e58f4ecf4aea858a1cf78a5ac77a
Source dataset
uspto-grants-2013_07
Patent number
US08486398B2

Reaction notes

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