Tetrabutylammonium Fluoride → HCID 86676331, compound

HRID 1023030Notes

Reaction equation

HRID 1023030 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([O:38][Si](C(C)(C)C)(C)C)[CH2:10][C:11]([C:14]1[N:15]=[C:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:37])[CH2:26][N:27]3[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:36])([F:35])[F:34])=[N:28]3)[CH2:21][CH2:20]2)[S:17][CH:18]=1)=[N:12][OH:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([OH:38])[CH2:10][C:11]([C:14]1[N:15]=[C:16]([CH:19]2[CH2:20][CH2:21][N:22]([C:25](=[O:37])[CH2:26][N:27]3[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:36])([F:35])[F:34])=[N:28]3)[CH2:23][CH2:24]2)[S:17][CH:18]=1)=[N:12][OH:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86676330HCID 86676330, compound2×

Product 1

HCID 86676331HCID 86676331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(2,6-difluorophenyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[2-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolyl]-1-propanone 1-oxime (i.e. the product of Example 6, Step B) (0.25 g, 0.37 mmol) in tetrahydrofuran (5 mL) was added a 1 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.55 mL). The resulting solution was stirred at room temperature for 2 h, concentrated under reduced pressure and treated with minimal dichloromethane and water. The resulting mixture was eluted on a Celite® extraction tube (ChemElute® diatomaceous earth-based liquid-liquid exchange cartridge) with dichloromethane and concentrated to provide 0.225 g of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiontreated with minimal dichloromethane and water
  3. washThe resulting mixture was eluted on a Celite® extraction tube (ChemElute® diatomaceous earth-based liquid-liquid exchange cartridge) with dichloromethane
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-81b449871a694696877652baa254b3ac
Source dataset
uspto-grants-2014_05
Patent number
US08722678B2

Reaction notes

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