Hydrochloric Acid → HCID 67772616, compound

HRID 1963085Notes

Reaction equation

HRID 1963085 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:20]3[N:21]=[CH:22][C:23](C(O)=O)=[CH:24][C:19]3=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]=2[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[C:36]=2[CH3:42])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.N1C2C(=CC=CC=2)C=CC=1.Cl.O1CCOCC1>[Cu]>[F:41][C:37]1[C:36]([CH3:42])=[C:35]([CH:40]=[CH:39][CH:38]=1)[CH2:34][C:17]1[C:18]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:19]2[CH:24]=[CH:23][CH:22]=[N:21][N:20]2[C:16]=1[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 312751,4-DioxaneHCID 70663716HCID 70663716, compound

Product 1

HCID 67772616HCID 67772616, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
170 °C

Procedure

A mixture of the compound of example 8, step 11 (0.057 g, 0.10 mmol), copper powder (0.007 g, 0.10 mmol) and quinoline (0.40 ml) was plunged into an oil bath pre-heated at 170° C. for 1.25 h. After cooling to room temperature and evaporation of the volatiles under reduced pressure, the residue was dissolved in EA (10 ml) and the solution washed with water and brine, dried over magnesium sulfate, filtered and concentrated to dryness. The obtained orange oil was purified by chromatography on silica gel (DCM/MOH, 100:0, then 90:10). The product was dissolved in 2 ml of DCM and a 4 N solution of hydrogen chloride in dioxane (0.25 ml, 0.98 mmol) was added. After stirring at room temperature overnight, the solution was evaporated to dryness. The obtained solid was triturated several times with diethyl ether and dried in vacuo at 50° C. to give 0.016 g of the title compound in the form of [6-(3-fluoro-2-methyl-benzyl)-5-phenyl-pyrrolo[1,2-b]pyridazin-7-yl]-piperazin-1-yl-methanone hydrochloride as an orange solid with the following characteristics:

Workup

  1. customwas plunged into an oil bath
  2. temperatureAfter cooling to room temperature
  3. customevaporation of the volatiles under reduced pressure
  4. dissolutionthe residue was dissolved in EA (10 ml)
  5. washthe solution washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe obtained orange oil was purified by chromatography on silica gel (DCM/MOH, 100:0
  10. dissolutionThe product was dissolved in 2 ml of DCM
  11. customthe solution was evaporated to dryness
  12. customThe obtained solid was triturated several times with diethyl ether
  13. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-e886f967125e4cdcb6f089d05f6baa21
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

Loading…