1-Hydroxybenzotriazole → HCID 178422957, compound

HRID 2396917Notes

Reaction equation

HRID 2396917 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=O.Cl.C([N:19]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([NH2:19])=[O:15]

Participants

6

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178422970HCID 178422970, compound

Product 1

HCID 178422957HCID 178422957, compoundYield 114.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid (3.06 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.17 g), and N-hydroxybenzotriazole (2.53 g) in N,N-dimethylformamide (45 ml) was stirred at 0° C. for 15 minutes. (2E,4E)- and (2Z,4E)-4-Methyl-2,4-heptadien-1-ylamine (2.35 g) was added to the solution. The solution was stirred at 0° C. for 2 hours and then at room temperature overnight. The reaction mixture was diluted with water. The resulting precipitate was filtered and washed with water to give N-[(2E,4E)- and (2Z,4E)-4-methyl-2,4-heptadien-1-yl]-4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxamide (3.5 g).

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-673feaccc85f4c93acde8e61fbb2f9dc
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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