Benzylamine → HCID 69354528, compound

HRID 1744242Notes

Reaction equation

HRID 1744242 reaction equation
C[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)[CH2:18][CH2:19][CH2:20][N:21]=[C:22]=NCC.O.ON1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.[CH2:38](N)[C:39]1C=CC=[CH:41][CH:40]=1>CN(C)C=O.O>[CH2:22]([N:21]([CH2:20][C:19]1[CH:18]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:12]([C:7]1[C:8](=[O:11])[NH:9][CH:10]=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=1)=[O:14])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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 69354528HCID 69354528, 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: C15H14N2O4−0.47H2O; Calcd: C, 61.12; H, 5.11; N, 9.50. Found: C, 61.17; H, 4.81; N, 9.71. (c) 2-Hydroxy-pyridine-3,5-dicarboxylic acid 5-methyl ester

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-43b0f627d26940b294f91f6e5cccbc91
Source dataset
uspto-grants-2006_03
Patent number
US07015237B2

Reaction notes

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