Tetrabutylammonium Fluoride → HCID 136127371, compound

HRID 2068896Notes

Reaction equation

HRID 2068896 reaction equation
[OH:1][CH2:2][C:3]1([CH3:49])[CH2:11][C:10]2[N:9](COCC[Si](C)(C)C)[N:8]=[C:7]([C:20]3[N:21](COCC[Si](C)(C)C)[C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[C:24]([N:29]([CH3:40])[C:30](=[O:39])[CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]3=[O:38])[CH:23]=4)[C:6]=2[CH2:5][CH2:4]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[OH:1][CH2:2][C:3]1([CH3:49])[CH2:11][C:10]2[NH:9][N:8]=[C:7]([C:20]3[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[C:24]([N:29]([CH3:40])[C:30](=[O:39])[CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]3=[O:38])[CH:23]=4)[C:6]=2[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58550127HCID 58550127, compound

Product 1

HCID 136127371HCID 136127371, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N-(2-{6-hydroxymethyl-6-methyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methyl-2-(2-oxopiperidin-1-yl)acetamide (63 mg, 0.09 mmol) in N,N-dimethylformamide (1.5 ml) was added to tetrabutylammonium fluoride (0.6 ml, 0.6 mmol) concentrated in advance under reduced pressure. Ethylenediamine (0.2 ml) was added, and the mixture was stirred with heating at 80° C. overnight. After cooling, water and ethyl acetate were added, and the organic layer was separated. Then, the organic layer was washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography to give the title compound (5.5 mg, yield 16%).

Workup

  1. concentrationconcentrated in advance under reduced pressure
  2. additionEthylenediamine (0.2 ml) was added
  3. temperatureAfter cooling
  4. additionwater and ethyl acetate were added
  5. customthe organic layer was separated
  6. washThen, the organic layer was washed successively with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. customSodium sulfate was removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by thin layer silica gel chromatography

Sources & evidence

ORD record
ord-af087fc56a6a4c11a66807ab38a66c45
Source dataset
uspto-grants-2012_10
Patent number
US08299070B2

Reaction notes

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