Formaldehyde → N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide

HRID 2080219Notes

Reaction equation

HRID 2080219 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1.C1C=C2C(C=C(NCNCCCC(O)=O)C=C2)=CC=1.C=O.[C:45]([O:48][CH2:49]C)(=O)C>CO>[CH2:15]([C:12]1[S:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([NH:1][CH2:45][O:48][CH3:49])=[N:3][CH:4]=2)=[CH:14][CH:13]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl Acetate2×HCID 1910612-Naphthylaminomethyl-gamma-aminobutyric acidHCID 231303536-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 23130744N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamideYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide described in Example A-144 (210 mg, 0.65 mmol) and 5,5-dimethylimidazo phospho-2,4-dione (92 mg, 0.71 mmol) in methanol (15 mL) was added an aqueous solution of 37% formaldehyde (2.5 mL) under reflux in three time, and the solution was stirred for 1 hour. NH silica gel was added to the reaction solution, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (210 mg, 0.57 mmol, 87.6%) was obtained as a white solid.

Workup

  1. temperatureunder reflux in three time
  2. additionNH silica gel was added to the reaction solution
  3. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-a07a50c3babf45bda94512c29e6abd41
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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