N,N-Dimethyl-1,3-propanediamine → HCID 59225188, compound

HRID 905645Notes

Reaction equation

HRID 905645 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24]OS(C)(=O)=O)=[CH:20][N:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][N:31]([CH3:36])[CH2:32][CH2:33][CH2:34][NH2:35].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:35][CH2:34][CH2:33][CH2:32][N:31]([CH3:36])[CH3:30])=[CH:20][N:19]=1)=[O:17])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 59225158HCID 59225158, compound

Product 1

HCID 59225188HCID 59225188, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-t-Butoxycarbonylaminophenyl)-5-methanesulfonyloxy methylpyridine-2-carboxylic acid amide (Reference Compound No. 4-1, 4.9 g, 12 mmol) was added to a suspension of N,N-dimethyl-1,3-propanediamine (3.0 mL, 24 mmol) and potassium carbonate (3.3 g, 24 mmol) in DMF (40 mL), and then the reaction mixture was stirred at room temperature for 6 hours. Saturated aqueous sodium hydrogen carbonate (100 mL) was added thereto, and then the whole was extracted with ethyl acetate (100 mL) twice. The organic layer was washed with water (100 mL) three times, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 1.9 g of the title reference compound as a yellow amorphous product. (Yield 38%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (100 mL) twice
  2. washThe organic layer was washed with water (100 mL) three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  6. customto give 1.9 g of the title reference compound as a yellow amorphous product

Sources & evidence

ORD record
ord-5c2d969ea0174fc78be5e95ab27fb170
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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