Triethylamine → HCID 59636766, compound

HRID 535678Notes

Reaction equation

HRID 535678 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[O:21][C:20]([C:23]([O-])=[O:24])=[CH:19][C:18]=3[CH:17]=[C:16]([F:26])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].F[B-](F)(F)F.[C:33]1(=O)[N:37](OC(N(C)C)=[N+](C)C)[C:36](=O)CC1.C(N(CC)CC)C.Cl.CNC>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[O:21][C:20]([C:23]([N:37]([CH3:33])[CH3:36])=[O:24])=[CH:19][C:18]=3[CH:17]=[C:16]([F:26])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 68787018HCID 68787018, compound

Product 1

HCID 59636766HCID 59636766, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium 7-(4-benzylpiperazin-1-yl)-5-fluorobenzofuran-2-carboxylate (0.86 g, 2.38 mmol) was dissolved in dry dimethylformamide (10 mL), 2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate (TSTU) (0.93 g, 3.10 mmol) was added followed by triethylamine (1.16 mL, 8.34 mmol). The reaction was stirred for 20 min then dimethylamine hydrochloride (0.78 g, 9.54 mmol) was added. The reaction was stirred at rt over night. The solvent was evaporated and water and dichloromethane were added. The layers were separated. The aqueous phase was extracted with dichloromethane (3×). The combined organic phases were washed with water (3×) and brine, dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography (SiO2; DCM/MeOH; 97/3) to give 0.62 g (68%) of the product.

Workup

  1. stirringThe reaction was stirred at rt over night
  2. customThe solvent was evaporated
  3. additionwater and dichloromethane were added
  4. customThe layers were separated
  5. extractionThe aqueous phase was extracted with dichloromethane (3×)
  6. washThe combined organic phases were washed with water (3×) and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude was purified by flash chromatography (SiO2; DCM/MeOH; 97/3)

Sources & evidence

ORD record
ord-d2437bf227e04b2d9429f5be1b245e2b
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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