Piperazin-2-one → HCID 50912873, compound

HRID 1942087Notes

Reaction equation

HRID 1942087 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)=[CH:9][N:10]=2)[N:7]=1.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][C:24]1=[O:29].[F-].[K+]>CN1C(=O)CCC1.CCOC(C)=O>[F:22][C:21]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[N:18]2)=[CH:13][C:12]=1[CH2:11][C:8]1[N:6]2[N:7]=[C:2]([N:26]3[CH2:27][CH2:28][NH:23][C:24](=[O:29])[CH2:25]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

6

Reactant 3

HCID 231360Piperazin-2-oneHCID 522689Potassium FluorideHCID 581475166-(6-Chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline2×

Product 1

HCID 50912873HCID 50912873, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
180 °C

Procedure

The title compound was prepared using 6-(6-chloro-imidazo[1,2-b]pyridazin-3-ylmethyl)-7-fluoro-quinoline (Intermediate J, 50 mg, 0.160 mmol), piperazin-2-one (80 mg, 0.799 mmol) and KF (27.9 mg, 0.480 mmol) were suspended in NMP (1.0 mL). The RM was stirred at 180° C. for 5 h. The mixture was diluted with EtOAc and washed with 1M NaHCO3 (1×) and water (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 foam (tR 2.88 min (conditions 5), MH+=377, 1H-NMR in DMSO-d6: 8.85 (d, 1H); 8.33 (d, 1H); 8.07 (s, 1H); 7.98 (d, 1H); 7.83 (d, 1H); 7.74 (m, 1H); 7.5 (s, 2H); 7.11 (d, 1H); 4.41 (s, 2H); 4.00 (s, 2H); 3.67 (m, 2H); 3.26 (m, 2H)).

Workup

  1. customThe title compound was prepared
  2. washwashed with 1M NaHCO3 (1×) and water (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-439db3cf0d884bd687c4f171159340c2
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

Loading…