Chlorosuccinimide → HCID 18950547, compound

HRID 1492401Notes

Reaction equation

HRID 1492401 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:22]=[N:23][N:24]=2)[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([Se]C3C=CC=CC=3)[CH2:9]2)[CH:7]=1.ClN1C(=O)CCC1=O.N12CCCN=C1CCCCC2>ClCCl>[CH3:1][C:2]1[C:3]2[N:4]([CH:22]=[N:23][N:24]=2)[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]=[CH:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 18950551HCID 18950551, compound

Product 1

HCID 18950547HCID 18950547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 387 mg of 1-(8-methyl-1,2,4-triazolo-[4,3-b]pyridazin-6-yl)-3-(phenylselenyl)-4-piperidinol in dichloromethane at room temperature was treated with a solution of 147 mg of N-chlorosuccinimide in 3 ml of dichloromethane and stirred at room temperature. A white precipitate formed. After 15 minutes, 305 mg of 1,8-diazabicyclo [5,4,0]undec-7-ene was added and stirring continued at room temperature for 20 hours. This resulted in a very dark-colored solution. The reaction volume was reduced at the rotary evaporator and the solution put directly on a silica gel (20 g) flash chromatography column. After rinsing the material on the column with dichloromethane, it was eluted with 95% dichloromethane/5% ethanol (10% concentrated ammonium hydroxide). The clean fractions were combined to give, on evaporation of the solvent, a tan viscous oil which slowly crystallized to give 1-(8-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-1,4,5,6-tetrahydro-4-pyridinol melting at about 171°-173° C.

Workup

  1. customA white precipitate formed
  2. stirringstirring
  3. waitcontinued at room temperature for 20 hours
  4. customThis resulted in a very dark-colored solution
  5. customThe reaction volume was reduced at the rotary evaporator
  6. washAfter rinsing the material on the column with dichloromethane, it
  7. washwas eluted with 95% dichloromethane/5% ethanol (10% concentrated ammonium hydroxide)
  8. customto give, on evaporation of the solvent
  9. customa tan viscous oil which slowly crystallized

Sources & evidence

ORD record
ord-f3430951586f4585ae5187ce5573c1ea
Source dataset
uspto-grants-1994_12
Patent number
US05374632

Reaction notes

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