Dicyclohexylcarbodiimide → HCID 44250361, compound

HRID 2189475Notes

Reaction equation

HRID 2189475 reaction equation
N1C=[C:5]([CH2:7][O:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:4]=[CH:3][CH:2]=1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25]([OH:27])=O)=[CH:17]1.C1CC[CH:31]([N:34]=C=NC2CCCCC2)CC1>CN(C=O)C>[N:34]1[CH:31]=[CH:2][CH:3]=[CH:4][C:5]=1[CH2:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:25]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:16][CH:17]=2)=[O:27])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 69867Indole-3-Carboxylic AcidHCID 21114566HCID 21114566, compound

Product 1

HCID 44250361HCID 44250361, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The 6-(pyridine-5-ylmethoxy)-pyridine-3-ylamine (114 mg, 0.57 mmol) and indole-3-carboxylic acid (91 mg, 0.57 mmol) were dissolved in DMF (3 ml), DCC (117 mg, 0.57 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 (44 mg, 23%) by chromatography (methanol:dichloromethane=2:30).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-8a8cf94465d7418d88f388463601eb00
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

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