Water → HCID 178507307, compound

HRID 1747498Notes

Reaction equation

HRID 1747498 reaction equation
C1CCN2C(=NCCC2)CC1.Cl.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:23]=[C:22]([NH2:24])[NH:21][N:20]=2)[CH2:15][CH2:14]1.[Cl:25][C:26]1[N:27]=[N:28][C:29](Cl)=[CH:30][CH:31]=1.O>CS(C)=O>[Cl:25][C:26]1[N:27]=[N:28][C:29]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[CH:23]=[C:22]([NH2:24])[NH:21][N:20]=3)[CH2:17][CH2:18]2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 673313,6-DichloropyridazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178479023HCID 178479023, compound

Product 1

HCID 178507307HCID 178507307, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,8-Diazabicyclo[5.4.0]-7-undecene (0.750 mL, 5.02 mmol) was added to a suspension of 3-(piperidin-4-yl)-1H-pyrazol-5-amine hydrochloride (0.400 g, 1.67 mmol) produced in Reference Example 33 in dimethyl sulfoxide (4 mL), and the mixture was stirred at room temperature for 10 minutes. Then, 3,6-dichloropyridazine (0.249 g, 1.67 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour and at 60° C. for 4 hours. After cooling to room temperature, water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: ethyl acetate/methanol=95/5-90/10 (gradient)] to obtain the title compound (0.330 g, yield: 71%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour and at 60° C. for 4 hours
  2. temperatureAfter cooling to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe obtained organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [elute: ethyl acetate/methanol=95/5-90/10 (gradient)]

Sources & evidence

ORD record
ord-a15d4b8c29c14cc68ed9d4abd4ae92bd
Source dataset
uspto-grants-2015_10
Patent number
US09150575B2

Reaction notes

Loading…