Ammonia → HCID 18677512, compound

HRID 1634206Notes

Reaction equation

HRID 1634206 reaction equation
CO[C:3](=O)[C:4]1[CH:9]=[C:8]([NH2:10])[N:7]=[C:6]([NH2:11])[CH:5]=1.[NH3:13]>>[NH2:13][CH2:3][C:4]1[CH:9]=[C:8]([NH2:10])[N:7]=[C:6]([NH2:11])[CH:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 111945474-Pyridinecarboxylic acid, 2,6-diamino-, methyl ester

Product 1

HCID 18677512HCID 18677512, compound

Conditions

Temperature
60 °C

Procedure

A compound of formula I-3 may be prepared as follows: A solution of 2,6-diamino-isonicotinic acid methyl ester (X) is treated for 1 hour with gaseous ammonia. The mixture is heated for 36 hours at about 60° C. in an autoclave and is then filtered through decalite. The obtained 2,6-diamino-isonicotinamide is suspended in THF and boran-dimethylsulfide-complex (or NaBH4) is added. The mixture is refluxed for 4 days. After cooling to room temperature HCl is added and the mixture is neutralized with NaOH, to give 4-aminomethyl-pyridine-2,6-diamine. A solution of this compound in pyridine is treated with a compound of formula XII together with a catalytic amount of 4-dimethylaminopyridine, and stirred for 2.5 hours at room temperature to obtain a compound of formula III. Furthermore, to the obtained solution of a compound of formula III in dioxane is added O-mesitylenesulfonylhydroxylamine and then an aldehyde of formula V. The mixture is heated to about 100° C. and after 2.5 hours KOH in methanol is added. After stirring the mixture at room temperature a compound of formula I-3 is obtained.

Workup

  1. customA compound of formula I-3 may be prepared
  2. filtrationis then filtered through decalite
  3. additionis added
  4. temperatureThe mixture is refluxed for 4 days
  5. temperatureAfter cooling to room temperature HCl
  6. additionis added

Sources & evidence

ORD record
ord-84db7cb120564cfaaa0dde9e7995576d
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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