Ethyl Acetate → HCID 50914920, compound

HRID 1942082Notes

Reaction equation

HRID 1942082 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@H:11]([C:13]3[CH:14]=[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+].CCO[C:29]([CH3:31])=[O:30]>CN1C(=O)CCC1>[F:22][C:21]1[CH:20]=[C:19]2[C:15]([CH:16]=[N:17][N:18]2[CH3:23])=[CH:14][C:13]=1[C@@H:11]([C:8]1[N:6]2[N:7]=[C:2]([N:10]3[CH2:9][CH2:8][N:6]([CH3:5])[C:29](=[O:30])[CH2:31]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 58147538HCID 58147538, compound2×

Product 1

HCID 50914920HCID 50914920, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

6-Chloro-3-[(S)-1-(6-fluoro-1-methyl-1H-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine (Intermediate E, 50.0 mg, 0.152 mmol), KF (26.4 mg, 0.455 mmol) and 1-methylperazine-2-one hydrochloride (51.9 mg, 0.455 mmol) were suspended in NMP (1 mL). The RM was stirred at 180° C. for 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 3.66 min (conditions 5), (tR 12.22 min (conditions 2), MH+=408.2, 1H-NMR in DMSO-d6: 7.92 (s, 1H); 7.83 (d, 1H); 7.49 (m, 3H); 7.11 (d, 1H); 4.78 (m, 1H); 4.00 (d, 1H); 3.95 (s, 3H); 3.86 (d, 1H); 3.67 (m, 2H); 3.30 (m, 2H); 2.80 (s, 3H); 1.71 (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-c8f15af01bb54bfcb950012e5b881c54
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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