Pyridazine → HCID 59367706, compound

HRID 515570Notes

Reaction equation

HRID 515570 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[Br:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[N:12][N:11]2[CH:27]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>C(Cl)(Cl)Cl.ClCCl>[Br:7][C:8]1[N:9]=[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)[CH2:18][CH2:17]3)=[N:12][N:11]2[C:27]=1[CH:32]1[CH:31]=[CH:30][N:29]([C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:28]=[CH:33]1

Participants

6

Reactant 3

HCID 9259PyridazineHCID 10928Ethyl chloroformateHCID 59367708HCID 59367708, compound

Product 1

HCID 59367706HCID 59367706, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1.3 g (12 mmol) of ethyl chloroformate are added, dropwise in 5 minutes, while cooling in an ice bath, to a mixture of 1.68 g (4.8 mmol) of 2-bromo-6-(4-pyrrolidin-1-ylpiperidin-1-yl)imidazo[1,2-b]pyridazine and 1.92 g (24 mmol) of pyridazine in 25 ml of chloroform. The mixture is stirred at ambient temperature for one hour and is then diluted with dichloromethane, and the solution is washed successively with a solution of sodium bicarbonate and then with a saturated solution of sodium chloride. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure after the addition of silica gel. The evaporation residue is loaded onto a silica gel column and the product is purified by silica gel column chromatography, elution being carried out with a mixture of 0 to 10% of methanol in dichloromethane. 1.93 g of product sufficiently pure for the rest of the synthesis are thus isolated.

Workup

  1. washthe solution is washed successively with a solution of sodium bicarbonate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionafter the addition of silica gel
  5. customthe product is purified by silica gel column chromatography, elution
  6. additionbeing carried out with a mixture of 0 to 10% of methanol in dichloromethane

Sources & evidence

ORD record
ord-cc866cb3ebf24fb4bad459fdfaba5f7c
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

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