Acetic Acid Mixture with Hydrobromic Acid → (S)-6-Bromo-N-(5-(2-methylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine hydrobromide

HRID 1024067Notes

Reaction equation

HRID 1024067 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[N:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][C@@H:19]3[CH3:31])=[CH:14][CH:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[BrH:32].CC(O)=O>>[BrH:32].[Br:32][C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][C@@H:19]3[CH3:31])=[CH:16][N:17]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86684144(S)-tert-Butyl 4-(6-(6-Chloroimidazo[1,2-b]pyridazin-8-ylamino)pyridin-3-yl)-3-methylpiperazine-1-carboxylate

Product 1

HCID 86684145(S)-6-Bromo-N-(5-(2-methylpiperazin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine hydrobromideYield 65%

Conditions

Temperature
150 °C

Procedure

An autoclave was charged with 115c (1.60 g, 3.6 mmol) and HBr/AcOH (60 mL). It was heated at 150° C. for 18 h. The reaction mixture was concentrated under reduced pressure to give black oil. The oil was recrystallized with methanol (30 mL)/dichloromethane (30 mL)/petroleum ether (90 mL) to afford 115d as a yellow solid (1.1 g, 65%). MS-ESI: [M+H]+ 388.1

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give black oil
  3. customThe oil was recrystallized with methanol (30 mL)/dichloromethane (30 mL)/petroleum ether (90 mL)

Sources & evidence

ORD record
ord-05f6d1a9ee254ea79ca29d805b40b761
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

Loading…