1-Hydroxybenzotriazole → 5-Chloro-2-([(2-oxo-2-([4-(pyridin-4-yl)phenyl]amino)ethoxy)acetyl]amino)benzoic acid

HRID 1963982Notes

Reaction equation

HRID 1963982 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][O:11][CH2:12][C:13]([OH:15])=O)=[C:4]([C:17]([O:19]C)=[O:18])[CH:3]=1.[N:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][O:11][CH2:12][C:13](=[O:15])[NH:31][C:30]2[CH:29]=[CH:28][C:27]([C:24]3[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=3)=[CH:33][CH:32]=2)=[C:4]([CH:3]=1)[C:17]([OH:19])=[O:18]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 15126544-(Pyridin-4-yl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 510399542-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acid

Product 1

HCID 442325235-Chloro-2-([(2-oxo-2-([4-(pyridin-4-yl)phenyl]amino)ethoxy)acetyl]amino)benzoic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.75 g (2.5 mmol) of (2-([4-chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethoxy)acetic acid, 0.43 g (2.5 mmol) of 4-(pyridin-4-yl)aniline, 0.58 g (3.0 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 0.41 g (3.0 mmol) of 1-hydroxybenzotriazole were stirred in 5.3 mL of DMA for 2 hours. After completion of the reaction, the reaction solution was introduced into an aqueous sodium bicarbonate solution. The solid was separated by filtration, and washed with water to give 0.96 g of 5-chloro-2-([(2-oxo-2-([4-(pyridin-4-yl)phenyl]amino)ethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 85%).

Workup

  1. customAfter completion of the reaction
  2. customThe solid was separated by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-d83b61fa65724613988335ae307054e3
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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