HCID 59406956, compound → 4-[2-(4-Fluorophenyl)-6-piperazin-1-ylimidazo[1,2-b]pyridazin-3-yl]pyrid-2-ylamine

HRID 1803888Notes

Reaction equation

HRID 1803888 reaction equation
C(=[N:14][C:15]1[CH:20]=[C:19]([C:21]2[N:25]3[N:26]=[C:27]([N:30]4[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)[CH:28]=[CH:29][C:24]3=[N:23][C:22]=2[C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[CH:18]=[CH:17][N:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1>Cl>[F:49][C:46]1[CH:47]=[CH:48][C:43]([C:22]2[N:23]=[C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]4)=[N:26][N:25]3[C:21]=2[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([NH2:14])[CH:20]=2)=[CH:44][CH:45]=1

Participants

3

Reactant 1

HCID 59406956HCID 59406956, compound

Product 1

HCID 251832934-[2-(4-Fluorophenyl)-6-piperazin-1-ylimidazo[1,2-b]pyridazin-3-yl]pyrid-2-ylamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 0.80 (1.22 mmol) of tert-butyl 4-[3-[2-(benzhydrylideneamino)pyrid-4-yl]-2-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]piperazine-1-carboxylate in 70 mL of aqueous hydrochloric acid is maintained at 80° C. for about 1 hour 30 minutes. After cooling, the aqueous phase is washed twice with diethyl ether and then basified by addition of ice-cold aqueous ammonia. The product is extracted with chloroform and the organic phase obtained is washed with water, dried over sodium sulfate and filtered, and the filtrate is concentrated under reduced pressure. The brown solid obtained is purified by chromatography on silica gel (35 g), eluting with a mixture of dichloromethane, methanol and aqueous ammonia (90/10/1). The product obtained is crystallized from 20 mL of refluxing acetonitrile to give 0.38 g of a white powder after cooling, filtering off and drying.

Workup

  1. temperatureAfter cooling
  2. washthe aqueous phase is washed twice with diethyl ether
  3. additionbasified by addition of ice-cold aqueous ammonia
  4. extractionThe product is extracted with chloroform
  5. customthe organic phase obtained
  6. washis washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. customThe brown solid obtained
  11. customis purified by chromatography on silica gel (35 g)
  12. washeluting with a mixture of dichloromethane, methanol and aqueous ammonia (90/10/1)
  13. customThe product obtained
  14. customis crystallized from 20 mL of refluxing acetonitrile

Sources & evidence

ORD record
ord-2e2cab26b00547bcb164a9af189433f8
Source dataset
uspto-grants-2013_01
Patent number
US08354405B2

Reaction notes

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