Potassium Fluoride → HCID 44512396, compound

HRID 1807759Notes

Reaction equation

HRID 1807759 reaction equation
C([Si](C)(C)[O:6][C:7]([C:16]1[CH:48]=[CH:47][C:19]([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([C:27]([C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][CH:39]4[CH2:44][CH2:43][S:42](=[O:45])[CH2:41][CH2:40]4)=[O:37])=[C:31]([F:46])[CH:30]=3)=[O:28])[CH2:23][CH2:22]2)=[CH:18][CH:17]=1)([C:12]([F:15])([F:14])[F:13])[C:8]([F:11])([F:10])[F:9])(C)(C)C.[F-].[K+]>O1CCCC1>[F:46][C:31]1[CH:30]=[C:29]([C:27]([N:24]2[CH2:25][CH2:26][N:21]([CH2:20][C:19]3[CH:47]=[CH:48][C:16]([C:7]([OH:6])([C:8]([F:11])([F:9])[F:10])[C:12]([F:13])([F:14])[F:15])=[CH:17][CH:18]=3)[CH2:22][CH2:23]2)=[O:28])[CH:34]=[CH:33][C:32]=1[NH:35][C:36]([NH:38][CH:39]1[CH2:44][CH2:43][S:42](=[O:45])[CH2:41][CH2:40]1)=[O:37]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 59175859HCID 59175859, compound

Product 1

HCID 44512396HCID 44512396, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 1-[4-(4-{4-[1-(tert-butyl-dimethyl-silanyloxy)-2,2,2-trifluoro-1-trifluoromethyl-ethyl]-benzyl}-piperazine-1-carbonyl)-2-fluoro-phenyl]-3-(1-oxo-tetrahydro-thiopyran-4-yl)-urea (0.173 mmol, 130 mg) in tetrahydrofuran (1 mL) was added potassium fluoride (50% wt on celite) (1.727 mmol, 201 mg). The resulting suspension was heated to 80° C. for 48 hours. The reaction mixture was filtered through celite and purified by SCX chromatography to afford the title compound (20 mg). MS (ESI) m/z 639.0 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. custompurified by SCX chromatography

Sources & evidence

ORD record
ord-31355a6c89e94ebc9c11faf1f2b1df11
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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