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

HRID 68186Notes

Reaction equation

HRID 68186 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-ae4dd99dba9341e4a5d8256d9cc01b94
Source dataset
uspto-grants-2014_09
Patent number
US08821871B2

Reaction notes

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