Triethylamine → 7-(4-(2-(Pyridin-2-yl)ethyl)piperazin-1-yl)-N-(pyridin-2-ylmethyl)benzofuran-2-carboxamide

HRID 535631Notes

Reaction equation

HRID 535631 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[C:23]3[O:22][C:21]([C:24]([O-])=[O:25])=[CH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.[Li+].[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.C(N(CC)CC)C.[N:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[CH2:61][NH2:62]>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]2[C:23]3[O:22][C:21]([C:24]([NH:62][CH2:61][C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][N:55]=4)=[O:25])=[CH:20][C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 68787401Lithium 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate

Product 1

HCID 596367727-(4-(2-(Pyridin-2-yl)ethyl)piperazin-1-yl)-N-(pyridin-2-ylmethyl)benzofuran-2-carboxamideYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium 7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxylate (0.060 g, 0.17 mmol) was dissolved in dry DMF (1.7 mL), and then TSTU (0.064 g, 0.21 mmol) was added followed by triethylamine (0.059 mL, 0.43 mmol). The reaction was stirred for 15 min then 2-picolylamine (0.019 mL, 0.19 mmol) was added. The reaction was stirred at room temperature under argon over night. The crude product was purified by preparative LC. The fractions were combined and the acetonitrile was evaporated. DCM was added and the layers separated. The aq phase was extracted with DCM (3×). The combined organic phases were dried (Na2SO4), filtered and evaporated to give 37 mg (49%) of the title compound.

Workup

  1. stirringThe reaction was stirred at room temperature under argon over night
  2. customThe crude product was purified by preparative LC
  3. customthe acetonitrile was evaporated
  4. additionDCM was added
  5. customthe layers separated
  6. extractionThe aq phase was extracted with DCM (3×)
  7. dry with materialThe combined organic phases were dried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-45b73daa7532418faffa5abcd799e7b9
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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