Pivaloyl chloride → 1-[4-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazin-1-yl]-2,2-dimethyl-propan-1-one

HRID 870751Notes

Reaction equation

HRID 870751 reaction equation
CCN(C(C)C)C(C)C.Cl.Cl.[Br:12][C:13]1[N:17]2[N:18]=[C:19]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.[C:28](Cl)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>C(OCC)(=O)C>[Br:12][C:13]1[N:17]2[N:18]=[C:19]([N:22]3[CH2:23][CH2:24][N:25]([C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:26][CH2:27]3)[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 866964333-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

Product 1

HCID 866964571-[4-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazin-1-yl]-2,2-dimethyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hunig's base [7087-99-5] (1.8 mL, 10.3 mmol) was added to an ambient temperature stirred suspension of 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride (907.1 mg, 2.6 mmol) in ethyl acetate (50 mL). After 30 minutes, pivaloyl chloride [3282-30-2] (0.3 mL, 2.5 mmol) was added and the suspension stirred under N2 blanket for 17 h then washed with brine, dried (MgSO4), and diluted with heptane. Chilling the stirred solution crystallized out a white powder which was isolated by filtration, 618.5 mg. LRMS (ESI) m/z 366.0/368.0 [(M+H)]+, calc'd for C16H20BrN6O: 366.26.

Workup

  1. stirringthe suspension stirred under N2 blanket for 17 h
  2. washthen washed with brine
  3. dry with materialdried (MgSO4)
  4. additiondiluted with heptane
  5. temperatureChilling the stirred solution
  6. customcrystallized out a white powder which
  7. customwas isolated by filtration, 618.5 mg

Sources & evidence

ORD record
ord-b71501f14ae74dfbb8470b6cfcb65c8d
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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