Tetrabutylammonium Fluoride Trihydrate → HCID 11618730, compound

HRID 229345Notes

Reaction equation

HRID 229345 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([NH:12][C:13]([CH3:32])([C:15](=[O:31])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C:24]3=[O:29])=[C:19]([CH3:30])[CH:18]=2)[CH3:14])=[O:11])=[CH:7][CH:6]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[C:4]([C:5]1[S:9][C:8]([C:10]([NH:12][C:13]([CH3:32])([C:15](=[O:31])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C:24]3=[O:29])=[C:19]([CH3:30])[CH:18]=2)[CH3:14])=[O:11])=[CH:7][CH:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 68872873HCID 68872873, compound

Product 1

HCID 11618730HCID 11618730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.81 g (1.63 mmol) of 5-(2-trimethylsilylethynyl)-N-{1-methyl-1-[3-methyl-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]ethyl}thiophene-2-carboxamide and 0.57 g (1.79 mmol) of tetrabutylammonium fluoride trihydrate in 30 ml of methylene chloride is stirred for 2 h and then the organic phase is washed 3× with water, dried with sodium sulphate, filtered and concentrated in vac. The crude product is purified by chromatography (silica gel, methylene chloride→methylene chloride:ethanol 25:1).

Workup

  1. washthe organic phase is washed 3× with water
  2. dry with materialdried with sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vac
  5. customThe crude product is purified by chromatography (silica gel, methylene chloride→methylene chloride:ethanol 25:1)

Sources & evidence

ORD record
ord-00fab7f8ead24bfdb19f5f166c1c60d0
Source dataset
uspto-grants-2009_07
Patent number
US07563786B2

Reaction notes

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