Methyl(2-pyridylmethyl)amine → HCID 57050861, compound

HRID 2299028Notes

Reaction equation

HRID 2299028 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:25]2[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]2=[O:35])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]([O:15]N2C3C=CC=CC=3N=N2)=O)[N:10]=[CH:9]1.[CH3:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>CN(C=O)C.C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([N:25]2[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]2=[O:35])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]([N:37]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)[CH3:36])=[O:15])[N:10]=[CH:9]1

Participants

5

Reactant 2

HCID 88757Methyl(2-pyridylmethyl)amineHCID 57232508HCID 57232508, compound

Product 1

HCID 57050861HCID 57050861, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-[(5S)-3-(3-fluoro-4-(4-(1-benzotriazolyloxy)carbonylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (prepared as detailed for Exarnples 49-80; 243 mg, 0.5 mM) dissolved in DMF (4 ml) was treated with 2-(N-methylaminomethyl)pyridine (68 mg, 0.55mM). The mixture was stirred under nitrogen, and heated to 55° for 18 hours. After cooling, the mixture was diluted with saturated sodium bicarbonate solution (20 ml), extracted with ethyl acetate (2×10 ml), the extract washed with water and dried over magnesium sulfate. After evaporation the residue was dissolved in dichloromethane and the solution chromatographed on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 20% methanol in dichloromethane. Relevant fractions were combined and evaporated to give title product (52 mg).

Workup

  1. temperatureheated to 55° for 18 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. washthe extract washed with water
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation the residue
  7. dissolutionwas dissolved in dichloromethane
  8. customthe solution chromatographed on a 10 g silica Mega Bond Elut® column
  9. washeluting with a gradient
  10. temperatureincreasing in polarity from 0 to 20% methanol in dichloromethane
  11. customevaporated

Sources & evidence

ORD record
ord-eb96cebdf758486fb541f375ddd1ebd8
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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