Water → 2-(2-Benzyloxy-acetylamino)-nicotinamide

HRID 2100458Notes

Reaction equation

HRID 2100458 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH2:11]([O:18][CH2:19][C:20](Cl)=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C1COCC1>[CH2:11]([O:18][CH2:19][C:20]([NH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 177085Benzyloxyacetyl chlorideHCID 5066232-Aminopyridine-3-carboxamide

Product 1

HCID 426324782-(2-Benzyloxy-acetylamino)-nicotinamideYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 2-amino-nicotinamide (100 mg, 0.7 mmol) in THF (5 ml) was added dropwise benzyloxyacetyl chloride [19810-31-2] (127 μL, 0.8 mmol) in THF (2 ml) at 5° C. The reaction mixture was heated to reflux for 2 hours. Water was added, the phases were separated and the inorganic layer was extracted with EtOAc (3 times). The combined organic layers were washed with brine, dried over Na2SO4, filtrated and concentrated in vacuo. Column chromatography on silica gel with CH2Cl2:MeOH 9:1 as eluent yielded 2-(2-benzyloxy-acetylamino)-nicotinamide (76 mg, 36%), MS(m/e): 286.1 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customthe phases were separated
  4. extractionthe inorganic layer was extracted with EtOAc (3 times)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltrated
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac35604ef01842b88305b87727f44ca8
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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