Potassium Fluoride → 1-(2-Chloro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(2-hydroxy-2-methylpropyl)urea

HRID 1807734Notes

Reaction equation

HRID 1807734 reaction equation
[Si]([O:8][C:9]([C:18]1[CH:48]=[CH:47][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][CH2:41][C:42]([OH:45])([CH3:44])[CH3:43])=[O:39])=[C:33]([Cl:46])[CH:32]=3)=[O:30])[CH2:25][CH2:24]2)=[CH:20][CH:19]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])(C(C)(C)C)(C)C.[F-].[K+]>O1CCCC1>[Cl:46][C:33]1[CH:32]=[C:31]([C:29]([N:26]2[CH2:25][CH2:24][N:23]([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([C:9]([OH:8])([C:14]([F:16])([F:15])[F:17])[C:10]([F:12])([F:13])[F:11])=[CH:48][CH:47]=3)[CH2:28][CH2:27]2)=[O:30])[CH:36]=[CH:35][C:34]=1[NH:37][C:38]([NH:40][CH2:41][C:42]([OH:45])([CH3:43])[CH3:44])=[O:39]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 86638553HCID 86638553, compound

Product 1

HCID 445119161-(2-Chloro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(2-hydroxy-2-methylpropyl)ureaYield 34.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 1-(4-(4-(4-(2-(tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)piperazine-1-carbonyl)-2-chlorophenyl)-3-(2-hydroxy-2-methylpropyl)urea (0.262 mmol, 190 mg) in tetrahydrofuran (1 mL) was added potassium fluoride (50% weight on celite) (0.524 mmol, 60.9 mg). The resulting suspension was stirred at room temperature for 16 hours. The reaction mixture was filtered through celite and concentrated under vacuum. The resulting residue was purified by SCX chromatography, followed by column chromatography (5-10% methanol in dichloromethane) to afford the title compound (55.5 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under vacuum
  3. customThe resulting residue was purified by SCX chromatography

Sources & evidence

ORD record
ord-c7ceeb905f714eabbffb40866a8e852b
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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