Water → HCID 44325576, compound

HRID 1916571Notes

Reaction equation

HRID 1916571 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1.O>C1COCC1>[Cl:11][C:12]1[N:13]=[N:14][C:15]([O:3][CH2:4][CH2:5][N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 762881-Pyrrolidineethanol

Product 1

HCID 44325576HCID 44325576, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

175 mg (4.01 mmol, 55%) NaH are added to a solution of 0.50 mL (4.04 mmol) N-(2-hydroxyethyl)pyrrolidine in 50 mL THF at 0° C. The reaction solution is stirred for 60 min and heated to RT. 500 mg (3.26 mmol) 3,6-dichloro-pyridazine are added. The solution is stirred for 5 h at RT. 50 mL water are added and the aqueous phase is extracted with 100 mL EtOAc. The organic phase is extracted once with saturated NaCl solution and dried over Na2SO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (gradient: EtOAc to EtOAc/MeOH/NH3 9:1:0.1).

Workup

  1. stirringThe solution is stirred for 5 h at RT
  2. extractionthe aqueous phase is extracted with 100 mL EtOAc
  3. extractionThe organic phase is extracted once with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customand further purification

Sources & evidence

ORD record
ord-e8f94771b4f441709db0e9da4bed8860
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…