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

HRID 870728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870728
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.)

Quellen und Nachweise

ORD-Eintrag
ord-0892f9b3568a4f0599831a4389682aba
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969565B2

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