Piperazine → HCID 50914337, compound

HRID 1942068Notes

Reaction equation

HRID 1942068 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@H:11]([C:13]3[C:14]([F:24])=[C:15]4[C:20](=[CH:21][C:22]=3[F:23])[N:19]=[CH:18][CH:17]=[CH:16]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CN1C(=O)CCC1.CCOC(C)=O>[F:24][C:14]1[C:13]([C@@H:11]([C:8]2[N:6]3[N:7]=[C:2]([N:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH3:12])=[C:22]([F:23])[CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2

Participants

6

Reactant 3

HCID 4837PiperazineHCID 522689Potassium FluorideHCID 58147525HCID 58147525, compound2×

Product 1

HCID 50914337HCID 50914337, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

6-[(S)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline (Intermediate B, 200 mg, 0.569 mmol), KF (371 mg, 6.26 mmol) and piperazine (490 mg, 5.69 mmol) were suspended in NMP (2.85 mL). The RM was stirred at 170° C. for 1 h. The mixture was diluted with EtOAc and washed with 1M Na2CO3 (1×) and water (2×). The aqueous was further extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography and afforded the title compound as a yellow foam (tR 2.78 min (conditions 1), MH+=395, 1H-NMR in DMSO-d6: 8.95 (d, 1H); 8.45 (d, 1H); 7.77 (d, 1H); 7.61 (d, 1H); 7.59 (s, 1H); 7.58 (m, 1H); 7.02 (d, 1H); 4.95 (m, 1H); 3.23 (m, 2H); 3.07 (m, 2H); 2.62 (m, 2H); 2.56 (m, 2H); 1.87 (d, 3H)).

Workup

  1. washwashed with 1M Na2CO3 (1×) and water (2×)
  2. extractionThe aqueous was further extracted with EtOAc (2×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6907f41264bb4b0892c7d92d0a53ce24
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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