Water → HCID 23130543, compound

HRID 2080223Notes

Reaction equation

HRID 2080223 reaction equation
C(O[CH2:4][NH:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([NH:12][CH2:13][C:14]2[S:15][C:16]([O:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:8][N:7]=1)C.[BH4-].[Na+].O.C(OCC)(=O)C>CS(C)=O>[CH3:4][NH:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([NH:12][CH2:13][C:14]2[S:15][C:16]([O:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 23130654HCID 23130654, compound

Product 1

HCID 23130543HCID 23130543, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6-(ethoxymethyl-amino)-N-(5-m-tolyloxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-155 (70 mg, 0.17 mmol) in dimethylsulfoxide (5 mL) was added sodium borohydride (20 mg, 0.51 mmol), and the solution was stirred for 20 minutes at 120° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with brine once. The organic layer was passed through a glass filter lined with NH silica gel, and eluted thoroughly with ethyl acetate. The solvent was evaporated in vacuo, and the title compound (53 mg, 0.15 mmol, 88.2%) was obtained as a light brown solid.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with brine once
  3. filtrationfilter
  4. washeluted thoroughly with ethyl acetate
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ddcb3022746141ceb7e6c185e4d10022
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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