Ammonia → 6-Aminomethyl-4-ethoxy-N-methylnicotinamide

HRID 249718

Reaction equation

HRID 249718 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([C:16](=[O:19])[NH:17][CH3:18])=[CH:9][N:8]=1)(=O)=O.[NH3:20]>CO>[NH2:20][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([C:16]([NH:17][CH3:18])=[O:19])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 577913154-Ethoxy-5-methylcarbamoylpyridin-2-ylmethyl methanesulfonate

Product 1

HCID 577912976-Aminomethyl-4-ethoxy-N-methylnicotinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Ethoxy-5-methylcarbamoylpyridin-2-ylmethyl methanesulfonate (436 mg), dissolved in abs. MeOH (7 ml), was added dropwise to a methanolic ammonia solution (7.1 ml; 7N) in a microwave vessel at RT and with stirring in the course of 10 min. After standing overnight, the solvent was stripped off and the residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed from the acetonitrile and freeze-dried. The product was treated with saturated sodium chloride solution and rendered alkaline with potassium carbonate. After extraction with methylene chloride, the combined organic phases were dried with sodium sulfate, filtered and concentrated. 71 mg of the title compound were obtained.

Workup

  1. waitAfter standing overnight
  2. customthe residue was purified by means of preparative HPLC
  3. customfreeze-dried
  4. additionThe product was treated with saturated sodium chloride solution
  5. extractionAfter extraction with methylene chloride
  6. dry with materialthe combined organic phases were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a36aaf2c062e4b11ab9cb33213235253
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Linked notes

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