1,8-Diazabicyclo(5.4.0)undec-7-ene → (3-Chloro-4-{methyl-[2-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)ethyl]amino}-pyridin-2-yl)-methanol

HRID 1637638Notes

Reaction equation

HRID 1637638 reaction equation
[Cl:1][C:2]1[C:3]([CH2:13][OH:14])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:10][CH2:11]Cl)[CH3:9].[N+:15]([C:18]1[N:22]2[N:23]=[C:24]([SH:27])[CH:25]=[CH:26][C:21]2=[N:20][CH:19]=1)([O-:17])=[O:16].C1CCN2C(=NCCC2)CC1>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH2:13][OH:14])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH3:9])[CH2:10][CH2:11][S:27][C:24]1[CH:25]=[CH:26][C:21]2[N:22]([C:18]([N+:15]([O-:17])=[O:16])=[CH:19][N:20]=2)[N:23]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53764863{3-Chloro-4-[(2-chloroethyl)methylamino]pyridin-2-yl}methanolHCID 178526776HCID 178526776, compound

Product 1

HCID 18799441(3-Chloro-4-{methyl-[2-(3-nitroimidazo[1,2-b]pyridazin-6-ylsulfanyl)ethyl]amino}-pyridin-2-yl)-methanolYield 71.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

0.33 g (1.28 mmol) of {3-chloro-4-[(2-chloro-ethyl)methylamino]pyridin-2-yl}methanol and 0.33 g (1.68 mmol) of 3-nitroimidazo[1,2-b]pyridazine-6-thiol are dissolved in 10 ml of anhydrous dimethylformamide under an argon atmosphere, and the solution is treated with 0.25 ml (1.53 mmol) of DBU and then stirred at 50° C for 5 h. It is then cooled to room temperature and diluted with ethyl acetate. The precipitate is filtered off, washed with ethyl acetate and diethyl ether and dried. 0.36 g (71%) of the title compound is isolated as a pale beige solid. M.p. 189-191° C.

Workup

  1. temperatureIt is then cooled to room temperature
  2. filtrationThe precipitate is filtered off
  3. washwashed with ethyl acetate and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-e458ba9dc41347879ebc40398d467444
Source dataset
uspto-grants-2000_03
Patent number
US06043242

Reaction notes

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