1-Acetylpiperazine → HCID 50913160, compound

HRID 1942098Notes

Reaction equation

HRID 1942098 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[C:13]([F:23])=[C:14]4[C:18](=[CH:19][C:20]=3[F:21])[N:17]([CH3:22])[N:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[C:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])[CH3:27]>CN1C(=O)CCC1.CCOC(C)=O>[F:23][C:13]1[C:12]([CH2:11][C:8]2[N:6]3[N:7]=[C:2]([N:32]4[CH2:33][CH2:34][N:29]([C:26](=[O:28])[CH3:27])[CH2:30][CH2:31]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)=[C:20]([F:21])[CH:19]=[C:18]2[C:14]=1[CH:15]=[N:16][N:17]2[CH3:22]

Participants

6

Reactant 3

HCID 837951-AcetylpiperazineHCID 522689Potassium FluorideHCID 581475346-chloro-3-((4,6-difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine2×

Product 1

HCID 50913160HCID 50913160, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
180 °C

Procedure

6-chloro-3-((4,6-difluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine (Intermediate T, 40.0 mg, 0.12 mmol), KF (34.8 mg, 0.6 mmol) and 1-acetylpiperazine (46.1 mg, 0.36 mmol) were suspended in NMP (0.3 mL). The RM was stirred at 180° C. for 3 h. The mixture was diluted with EtOAc and washed with NaHCO3 10% (2×) and water (4×). 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 light brown foam (tR 3.72 min (conditions 5), MH+=426.3, 1H-NMR in DMSO-d6: 8.16 (s, 1H); 7.80 (d, 1H); 7.46 (d, 1H); 7.27 (s, 1H); 7.10 (d, 1H); 4.27 (s, 2H); 3.98 (s, 3H); 3.50 (s, 6H); 3.44 (m, 2H); 2.03 (s, 3H)).

Workup

  1. washwashed with NaHCO3 10% (2×) and water (4×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2b62b44ab9454147857784d913e54434
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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