1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Aminopyridine-3-carboxamide

HRID 1927246Notes

Reaction equation

HRID 1927246 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:13]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>O.CS(C)=O>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:13])=[O:5]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 729302-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Product 1

HCID 5066232-Aminopyridine-3-carboxamideYield 52.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-Aminonicotinic acid (5.0 g), WSC (10 g), HOBt (7.3 g), ammonium chloride (5.8 g), diisopropylethylamine (28 g), and DMSO (100 mL) were stirred for 16 hours at room temperature. Water was added and then extraction was performed with ethyl acetate and THF. The organic layer was concentrated and purified by silica gel chromatography (ethyl acetate) to obtain the titled compound (2.6 g).

Workup

  1. extractionextraction
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-feb4d981aa5c469e96a25eac92566e95
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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