Nicotinic Acid → HCID 18977143, compound

HRID 2393750Notes

Reaction equation

HRID 2393750 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Br.[NH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][C:36](=[O:39])[NH:37][N:38]=2)=[CH:29][CH:28]=1.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[CH:35][C:36](=[O:39])[NH:37][N:38]=3)=[CH:29][CH:28]=2)=[O:9])[CH:3]=1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18977149HCID 18977149, compound

Product 1

HCID 18977143HCID 18977143, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

868 mg of nicotinic acid, 954 mg of N-hydroxybenzotriazole and triethylamine (1.23 ml) were added to a dimethylformamide solution (50 ml) containing 2.0 g of 6-[4-(4-aminobutoxy)phenyl]pyridazin-3(2H)-one hydrobromide. 1.35 g of 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide was added to the mixture at 0° C., and the resulting mixture was stirred at room temperature for 6 hours and then poured into ice water, and precipitated crystal was collected by filtration. The crystal was recrystallized from ethanol to obtain 1.75 g of 6-[4-(4-(pyridin-3-ylcarbonylamino)butoxy)phenyl]pyridazin-3(2H)-one.

Workup

  1. customprecipitated crystal
  2. filtrationwas collected by filtration
  3. customThe crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-5e3ec9c0d65d475eb4e0e0f5ab5b7671
Source dataset
uspto-grants-1998_09
Patent number
US05808065

Reaction notes

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