Nicotinic Acid → N-[4-(3-Fluoronaphthalen-2-yl)-6-imino-1,6-dihydro-1,3,5-triazin-2-yl]pyridine-3-carboximidic acid

HRID 1583868Notes

Reaction equation

HRID 1583868 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CS(Cl)(=O)=O.[NH2:15][C:16]1[N:21]=[C:20]([NH2:22])[N:19]=[C:18]([C:23]2[C:24]([F:33])=[CH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:17]=1>N1C=CC=CC=1>[NH2:22][C:20]1[N:21]=[C:16]([NH:15][C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)[N:17]=[C:18]([C:23]2[C:24]([F:33])=[CH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:19]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 31297Methanesulfonyl chlorideHCID 13373714HCID 13373714, compound

Product 1

HCID 11971098N-[4-(3-Fluoronaphthalen-2-yl)-6-imino-1,6-dihydro-1,3,5-triazin-2-yl]pyridine-3-carboximidic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Nicotinic acid (0.58 gram) was dissolved in 10 ml of pyridine, 0.27 gram of methanesulfonyl chloride was added thereto, the mixture was heated to reflux for thirty minutes, 0.5 gram of 2,4-diamino-6-(2-fluoro-3-naphthyl)-s-triazine was added, and the mixture was heated to reflux for four hours. After the reaction was completed, pyridine was evaporated, water was added to the residue, the resulting separated mass was subjected to a column chromatography using 100 grams of silica gel, and eluted with ethyl acetate-benzene (9:1) to afford 2-amino-4-nicotinoylamino-6-(2-fluoro-3-naphthyl)-s-triazine, colourless crystals, melting point 230° to 235° C. (with decomposition). The yield was 0.35 gram.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for thirty minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux for four hours
  5. custompyridine was evaporated
  6. additionwater was added to the residue
  7. customthe resulting separated mass
  8. washeluted with ethyl acetate-benzene (9:1)

Sources & evidence

ORD record
ord-05c9a79786474d0e97ed86b077b81c93
Source dataset
uspto-grants-1985_11
Patent number
US04554275

Reaction notes

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