Dimethylformamide → HCID 44251315, compound

HRID 2189469Notes

Reaction equation

HRID 2189469 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.CN(C(ON1N=[N:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:37][N:38]([CH:40]=[O:41])C>>[CH3:22][C:27]1[C:26]([O:41][C:40]2[N:38]=[CH:37][C:2]([NH:1][C:10]([C:2]3[NH:1][C:9]4[C:4]([CH:3]=3)=[CH:5][CH:6]=[CH:7][CH:8]=4)=[O:12])=[CH:3][CH:4]=2)=[CH:25][CH:24]=[CH:23][N:28]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 72899Indole-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 44251315HCID 44251315, compoundYield 14%

Conditions

Temperature
80 °C

Procedure

The bispyridine ester amine compound (120 mg, 0.62 mmol) in Example 1 and 1H-indole-2-carboxylic acid (100 ml, 0.62 mmol) were dissolved in DMF (5 ml), HBTU (240 mg, 0.62 mmol) was added to the solution, and 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 brown solid (30 mg, 14%) by chromatography (methanol:dichloromethane=1:30).

Workup

  1. washthe product was washed
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f2ca3e6191c9435396d5f35d717630d1
Source dataset
uspto-grants-2012_12
Patent number
US08324246B2

Reaction notes

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