5-Chloropyridine-2,3-diamine → HCID 178478271, compound

HRID 2218435Notes

Reaction equation

HRID 2218435 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN(C=O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:23]([C:22]3[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][N:10]4[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]4)=[CH:26][CH:25]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 12682545-Chloropyridine-2,3-diamineHCID 111838924-(2-(Piperidin-1-yl)ethoxy)benzaldehyde

Product 1

HCID 178478271HCID 178478271, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

5-Chloropyridin-2,3-diamine (0.200 g, 1.39 mmol) was dissolved in DMF (5 ml). Iron(III)chloride hexahydrate (0.025 g, 0.092 mmol) was added and the mixture heated to 80° C. 4-(2-Piperidin-1-ylethoxy)benzaldehyde (0.33 g, 1.41 mmol) dissolved in DMF (2 ml) was added dropwise, and the reaction mixture was heated at 120° C. for 5 h with air bubbling through the solution. The DMF was removed by evaporation and the solid residue was washed with 1M NaOH and diethyl ether. The crude product was purified by column chromatography (EtOAc/heptane, 1:1), giving the title product (0.017 g, 3%).

Workup

  1. additionwas added dropwise
  2. temperaturethe reaction mixture was heated at 120° C. for 5 h with air
  3. custombubbling through the solution
  4. customThe DMF was removed by evaporation
  5. washthe solid residue was washed with 1M NaOH and diethyl ether
  6. customThe crude product was purified by column chromatography (EtOAc/heptane, 1:1)

Sources & evidence

ORD record
ord-7de34dda10e0484b9b933c0ca498c76c
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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