Sodium Iodide → HCID 67206647, compound

HRID 1171802Notes

Reaction equation

HRID 1171802 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[C:16]([N:23]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].N12CCCN=C1CCCCC2.[I-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[C:19]([O:18][C:16]([N:23]1[CH2:27][CH2:26][CH:25]([NH:28][C:12]2[N:11]=[N:10][C:9]([C:7](=[O:8])[NH:6][CH2:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)=[CH:14][CH:13]=2)[CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27563701-Boc-3-aminopyrrolidineHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 67206647HCID 67206647, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.400 g, 1.77 mmol), 1-Boc-3-aminopyrrolidine (0.400 g, 2.1 mmol), tetrabutylammonium bromide (0.120 g, 0.36 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (1.000 g, 6.00 mmol) in 1,4-dioxane (30 mL) was heated under reflux overnight. A catalytic amount of sodium iodide was added and the heating was continued for 16 hours. The solvent was removed in vacuo and the residue was washed with 1 M citric acid (50 mL) and ethyl ether (50 mL) was added. Ultrasonication of the mixture followed by filtration afforded 3-[6-(2-cyclopropylethyl-carbamoyl)pyridazin-3-ylamino]pyrrolidine-1-carboxylic acid tert-butyl ester as a white solid in 81% yield (0.539 g) which was used for next step reaction without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed in vacuo
  4. washthe residue was washed with 1 M citric acid (50 mL) and ethyl ether (50 mL)
  5. additionwas added
  6. customUltrasonication of the mixture
  7. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-f0e86ed17a694badae59018db994c4c0
Source dataset
uspto-grants-2010_11
Patent number
US07829712B2

Reaction notes

Loading…