Dicyclohexylcarbodiimide → HCID 44250360, compound

HRID 2189474Notes

Reaction equation

HRID 2189474 reaction equation
[N:1]1[CH:6]=[C:5]([O:7][C:8]2[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:4]=[N:3][CH:2]=1.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24](O)=[O:25])=[CH:16]1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[N:3]1[CH:4]=[C:5]([O:7][C:8]2[N:13]=[CH:12][C:11]([NH:14][C:24]([C:17]3[C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[NH:15][CH:16]=3)=[O:25])=[CH:10][CH:9]=2)[CH:6]=[N:1][CH:2]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 689661066-[(Pyrimidin-5-yl)oxy]pyridin-3-amine

Product 1

HCID 44250360HCID 44250360, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The 6-(pyrimidine-5-yloxy)-pyridine-3-ylamine (53 mg, 0.28 mmol) and indole-3-carboxylic acid (45 mg, 0.28 mmol) were dissolved in DMF (5 ml), DCC (58 mg, 0.28 mmol) was added to the solution, and then the mixture was stirred at 80° C. for 8 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a white solid (55 mg, 59%) by chromatography (methanol:dichloromethane=2:30).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-55cbf320cb5e4a0f89348d1d7e298d9b
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

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