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

HRID 574105Notes

Reaction equation

HRID 574105 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-652de8d03ddc42a78150111980eaa109
Source dataset
uspto-grants-2015_05
Patent number
US09034822B2

Reaction notes

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