Isopropylamine → HCID 57697946, compound

HRID 1398068Notes

Reaction equation

HRID 1398068 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH:11]([NH2:14])([CH3:13])[CH3:12].C(P(O)(=O)O)CC.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:14][CH:11]([CH3:13])[CH3:12])=[O:8])=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 6363IsopropylamineHCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 204484Propylphosphonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 57697946HCID 57697946, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 300 mg (2.17 mmol) of 6-aminonicotinic acid in 50 mL of chloroform were added 370 μL (4.34 mmol) of isopropylamine, 4 mL of anhydrous propanephosphonic acid (25 wt % solution in ethyl acetate) and 1.4 mL (10 mmol) of triethylamine, and the mixture was stirred for 6 hours at room temperature. Then, saturated sodium bicarbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated saline solution and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=10/1 to 5/1) to give 30 mg (8%) of the title compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried over with anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=10/1 to 5/1)

Sources & evidence

ORD record
ord-d38514679db847399682c9dfcdc93d92
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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