Hydrochloric Acid → 3-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

HRID 870728Notes

Reaction equation

HRID 870728 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([Br:24])=[CH:22][N:23]=3)[N:20]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[ClH:1].[Br:24][C:21]1[N:19]2[N:20]=[C:15]([N:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)[CH:16]=[CH:17][C:18]2=[N:23][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 686481214-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866964333-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (6.4 mL) was added to a solution of 4-(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester 2.9 g, 7.6 mmol) in methanol (150 mL), allowed to stir at ambient temperature overnight, then evaporated to dryness. The resultant yellow solid was dissolved in methanol and the stirred solution diluted with diethyl ether to precipitate 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride as 2.6 g of white powder, mp. 275-276° C. (dec.). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.24 (br. s., 4H) 3.82-3.92 (m, 4H) 7.57 (d, J=10.11 Hz, 1H) 8.05 (s, 1H) 8.12 (d, J=10.10 Hz, 1H) 9.70 (br. s., 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm 41.86, 42.37, 101.30, 114.15, 124.22, 127.20, 134.76, 155.43. LRMS (ESI) m/z 282.1/284.1 [(M+H)]+, calc'd for C10H12BrN5: 282.14.

Workup

  1. customevaporated to dryness
  2. dissolutionThe resultant yellow solid was dissolved in methanol
  3. additionthe stirred solution diluted with diethyl ether
  4. customto precipitate 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride as 2.6 g of white powder, mp. 275-276° C. (dec.)

Sources & evidence

ORD record
ord-0892f9b3568a4f0599831a4389682aba
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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