Tetrabutylammonium Fluoride → N-[5-Methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-methanesulfonamide

HRID 1517080Notes

Reaction equation

HRID 1517080 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)[C:5]([N:21](S(C)(=O)=O)[S:22]([CH3:25])(=[O:24])=[O:23])=[N:6][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1)=[O:9].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=2)[C:5]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])=[N:6][C:7]=1[C:8]([N:10]1[CH2:11][CH2:12][CH:13]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:15]1)=[O:9]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57441126N-{5-Methyl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]-3-[3-(trifluoromethyl)phenyl]pyridin-2-yl}-N-(methylsulfonyl)methanesulfonamide2×

Product 1

HCID 57441147N-[5-Methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-methanesulfonamideYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.13 g (0.2 mmol) of N-{5-methyl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]-3-[3-(trifluoromethyl)phenyl]pyridin-2-yl}-N-(methylsulfonyl)methanesulfonamide (intermediate 4) in 2.0 ml of THF was added 0.2 ml (0.2 mmol) of a tetrabutylammonium fluoride solution (1M in THF) and the reaction mixture was subsequently heated up to reflux. After 4 days, the solvent was evaporated and the crude product purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1) to give 0.069 g (64%) of the title compound as yellow amorphous solid. MS: 511.3 (MH+).

Workup

  1. temperaturethe reaction mixture was subsequently heated up
  2. temperatureto reflux
  3. customthe solvent was evaporated
  4. customthe crude product purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1)

Sources & evidence

ORD record
ord-5d6fc428d65a482bb78d7233f9fbe682
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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