Water → N-(5-Benzyl-thiophen-2-ylmethyl)-6-methylamino-nicotinamide

HRID 2080222Notes

Reaction equation

HRID 2080222 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH2:23]OC)=[N:18][CH:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(OCC)(=O)C>CS(C)=O.CO>[CH2:1]([C:8]1[S:12][C:11]([CH2:13][NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH3:23])=[N:18][CH:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 4311764Sodium borohydrideHCID 23130744N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide

Product 1

HCID 23130402N-(5-Benzyl-thiophen-2-ylmethyl)-6-methylamino-nicotinamideYield 38.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of N-(5-benzyl-thiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide described in Example A-159 (183 mg, 0.52 mmol) in dimethylsulfoxide (3 mL) was added sodium borohydride (120 mg, 3.12 mmol), and the solution was stirred at 140° C. for 5 hours. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed with water twice. Silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=10:1), and the title compound (68 mg, 0.20 mmol, 38.8%) was obtained as a green solid.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. additionSilica gel was added to the organic layer
  4. customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record
ord-ff774ce0e8144e0980ad673ecd78825d
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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