Sodium Bicarbonate → HCID 22115594, compound

HRID 1276191Notes

Reaction equation

HRID 1276191 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](C(O)=O)[CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(C1NC=CN=1)(C1[NH:24]C=CN=1)=O.[C:33](=[O:36])([O-])O.[Na+]>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:33]([NH2:24])=[O:36])[CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 22115590HCID 22115590, compound

Product 1

HCID 22115594HCID 22115594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-methylpiperazin-1-yl)naphthalene-7-carboxylic acid (0.270 g, 1.00 mmol) in anhydrous tetrahydrofuran (5 mL) at room temperature was added carbonyl diimidazole (0.178 mg, 1.10 mmol, 1.1 eq) directly as a solid. The resulting reaction solution was stirred at room temperature under nitrogen for 3 hours. The appropriate amine (1.1 mmol, 1.1 eq) was then added, and the resulting reaction solution was stirred at room temperature under nitrogen for 16 hours. A saturated solution of sodium hydrogen carbonate was added, and the resulting aqueous mixture was extracted with ethyl acetate (2×25 mL). The organic extracts were combined, dried (MgSO4), and evaporated under reduced pressure. Column chromatography of the residue using silica gel (approximately 50 g) and an appropriate solvent system afforded the corresponding 1-(4-methylpiperazin-1-yl)naphthalene-7-carboxamide.

Workup

  1. customThe resulting reaction solution
  2. customthe resulting reaction solution
  3. stirringwas stirred at room temperature under nitrogen for 16 hours
  4. extractionthe resulting aqueous mixture was extracted with ethyl acetate (2×25 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a9c9ad86aeaf4d66bd1270eb21a44d41
Source dataset
uspto-grants-2000_12
Patent number
US06166020

Reaction notes

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