1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-Diaminopyridine-3-carboxamide

HRID 1927227Notes

Reaction equation

HRID 1927227 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CC[N:14]=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]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:14])=[O:5]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 189772452,6-Diaminonicotinic acid

Product 1

HCID 204748872,6-Diaminopyridine-3-carboxamideYield 73.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2,6-Diaminonicotinic acid (1.5 g), WSC (2.8 g), HOBt (2.0 g), ammonium chloride (1.6 g), diisopropylethylamine (7.6 g), and DMSO (45 mL) were stirred for 15 hours at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol=4:1). The organic layer thus obtained was concentrated and purified by NH silica gel column chromatography (ethyl acetate). Ethyl acetate and hexane were added to the residue thus obtained, and the solids were filtered off to obtain the titled compound (1.1 g).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by silica gel chromatography (ethyl acetate
  4. customThe organic layer thus obtained
  5. concentrationwas concentrated
  6. custompurified by NH silica gel column chromatography (ethyl acetate)
  7. additionEthyl acetate and hexane were added to the residue
  8. customthus obtained
  9. filtrationthe solids were filtered off

Sources & evidence

ORD record
ord-01050031bd7d42c6ae7a0e2674aca124
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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