Tetrabutylammonium Fluoride → N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(1-hydroxycyclopropyl)phenyl)propanamide

HRID 1842898Notes

Reaction equation

HRID 1842898 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:12](=[O:33])[CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([O:24][Si](C(C)(C)C)(C)C)[CH2:23][CH2:22]3)=[C:17]([F:32])[CH:16]=2)[CH3:14])[N:7]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:12](=[O:33])[CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3([OH:24])[CH2:23][CH2:22]3)=[C:17]([F:32])[CH:16]=2)[CH3:14])[N:7]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70816356N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-3-fluorophenyl)propanamide

Product 1

HCID 70816427N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(1-hydroxycyclopropyl)phenyl)propanamideYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-3-fluorophenyl)propanamide (141 mg, 0.240 mmol, 1 eq) in THF (2 mL) was added TBAF (c=1 mol/L in THF, 0.61 mL, 0.61 mmol, 2.6 eq) at room temperature and the mixture was stirred for 5 h after which the solvent was evaporated. The residue was purified by CC using EtOAc/cyclohexane 1:3 as eluent to yield N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(1-hydroxycyclopropyl)phenyl)propanamide (55 mg, 49%; TLC system: methanol/CHCl3 (1:9) Rf: 0.5).

Workup

  1. customwas evaporated
  2. customThe residue was purified by CC

Sources & evidence

ORD record
ord-f1b27e1c802a413da81e13b28c558620
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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