Potassium Fluoride → HCID 50914774, compound

HRID 1942078Notes

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+].OC(C(F)(F)F)=O.[C:34]1([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][C:41]2=[O:46])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN1C(=O)CCC1>[F:24][C:14]1[C:13]([CH:11]([C:8]2[N:6]3[N:7]=[C:2]([N:43]4[CH2:44][CH2:45][N:40]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[C:41](=[O:46])[CH2:42]4)[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

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-phenylpiperazin-2-one TFA salt (133 mg, 0.435 mmol) were suspended in NMP (483 μL). The RM was stirred at 180° C. for 5 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 1.0 min (conditions 4), MH+=485).

Workup

customThe mixture was purified by preparative UPLC with acetonitrile and water (+0.1% TFA) The fractions
customwere collected
customacetonitrile was removed
customThe solvent was removed
customa brown solid was obtained (tR 1.0 min (conditions 4), MH+=485)

Sources & evidence

ORD record: ord-302c5fe622514274989fb32b5309cec8
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389526B2

Reaction notes

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