1-Acetylpiperazine → HCID 50913158, compound

HRID 1942096Notes

Reaction equation

HRID 1942096 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:19](=[CH:20][C:21]=3[F:22])[N:18]([CH3:23])[N:17]=[CH:16]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].[C:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)(=[O:29])[CH3:28]>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:33]4[CH2:34][CH2:35][N:30]([C:27](=[O:29])[CH3:28])[CH2:31][CH2:32]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH3:12])=[C:21]([F:22])[CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][N:18]2[CH3:23]

Participants

6

Reactant 3

HCID 837951-AcetylpiperazineHCID 522689Potassium FluorideHCID 58147535HCID 58147535, compound2×

Product 1

HCID 50913158HCID 50913158, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
180 °C

Procedure

6-Chloro-3-[(S)-1-(4,6-difluoro-1-methyl-1H-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine (Intermediate Q, 36.6 mg, 0.105 mmol), KF (30.6 mg, 0.526 mmol) and 1-acetylpiperazine (40.5 mg, 0.316 mmol) were suspended in NMP (0.4 mL). The RM was stirred at 180° C. for 3.5 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 3.80 min (conditions 5), tR 13.31 min (conditions 3), MH+=440.3, 1H-NMR in DMSO-d6: 8.12 (s, 1H); 7.79 (d, 1H); 7.52 (s, 1H); 7.39 (d, 1H); 7.04 (d, 1H); 4.84 (m, 1H); 3.96 (s, 3H); 3.36 (m, 8H); 1.99 (s, 3H); 1.79 (d, 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-0afe8bd61d45423ab2da4bcaf911affd
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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