Dicyclohexylcarbodiimide → HCID 44250362, compound

HRID 2189476Notes

Reaction equation

HRID 2189476 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25](O)=[O:26])=[CH:17]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:25]([C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:16][CH:17]=3)=[O:26])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 180051666-[(6-Methyl-3-pyridinyl)oxy]-3-pyridinamine

Product 1

HCID 44250362HCID 44250362, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The 6-(6-methylpyridine-3-yloxy)-pyridine-3-amine (300 mg, 1.49 mmol) and indole-3-carboxylic acid (240 mg, 1.49 mmol) were dissolved in DMF (10 ml), DCC (280 mg, 1.49 mmol) was added to the solution, and then the mixture was stirred at 80° C. for 3 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a grey solid (340 mg, 66%) by chromatography (methanol:dichloromethane=1:30).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8b76756a08434973ab62d08af47e6106
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

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