Benzylamine → HCID 178498849, compound

HRID 1815886Notes

Reaction equation

HRID 1815886 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]([OH:14])=O)[C:8]([OH:11])=[N:9][CH:10]=1)=[O:4].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[C:7]([C:12](=[O:14])[NH:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:8]([OH:11])=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178498851HCID 178498851, compound

Product 1

HCID 178498849HCID 178498849, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-hydroxy-pyridine-3,5-dicarboxylic acid 5-methyl ester, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC. HCl 0.49 g, 2.6 mmol), 1-hydroxybenzotriazole hydrate (HOBT 0.35 g, 2.6 mmol), in dimethylformamide (10 ml) was added benzylamine 0.27 g (2.6 mmol). The mixture was stirred overnight at room temperature. Water was added (20 ml), and the mixture was filtered. The solid product was slurried in hot ethyl acetate to give 0.17 g (28% yield) of the title compound. MS: m/z (APCI, AP+) 287 [M.]+. CHN Analysis: C15H14N2O4.0.47 H2O; Calcd: C, 61.12; H, 5.11; N, 9.50. Found: C, 61.17; H, 4.81; N, 9.71.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-c8cdd36aa9bf42e6aa392dd381ae22d8
Source dataset
uspto-grants-2005_04
Patent number
US06881743B2

Reaction notes

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