Potassium Fluoride → HCID 50914773, compound

HRID 1942077Notes

Reaction equation

HRID 1942077 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH: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+].Cl.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH:31]([CH3:35])[C:30]1=[O:36]>CN1C(=O)CCC1>[F:24][C:14]1[C:13]([CH:11]([C:8]2[N:6]3[N:7]=[C:2]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[C:30](=[O:36])[CH:31]4[CH3:35])[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

5

Reactant 3

HCID 522689Potassium FluorideHCID 534070811,3-Dimethylpiperazin-2-one hydrochlorideHCID 58147541(Rac)-6-[1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline2×

Product 1

HCID 50914773HCID 50914773, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

(rac)-6-[1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-5,7-difluoro-quinoline (Intermediate C, 50 mg, 0.145 mmol), KF (84 mg, 1.450 mmol), 1,3-dimethylpiperazin-2-one HCl salt (75 mg, 0.435 mmol) were suspended in NMP (483 μL). The RM was stirred at 180° C. for 20 h. The mixture was purified by preparative UPLC with acetonitrile and water (+0.1% TFA) The fractions were collected and acetonitrile was removed. It was taken up with MeOH and passed through an SPE cartridge of PL-HCO3 MP from polymer lab. The solvent was removed and a brown solid was obtained (tR 0.9 min (conditions 4), MH+=437).

Workup

  1. customThe mixture was purified by preparative UPLC with acetonitrile and water (+0.1% TFA) The fractions
  2. customwere collected
  3. customacetonitrile was removed
  4. customThe solvent was removed
  5. customa brown solid was obtained (tR 0.9 min (conditions 4), MH+=437)

Sources & evidence

ORD record
ord-b84c80eb37a945fc9188f18d130421c8
Source dataset
uspto-grants-2013_03
Patent number
US08389526B2

Reaction notes

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