Tetrabutylammonium Fluoride → HCID 52936007, compound

HRID 2041743Notes

Reaction equation

HRID 2041743 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH2:20][OH:21])[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=2)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68161807HCID 68161807, compound

Product 1

HCID 52936007HCID 52936007, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-acetyl-6-[1-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-N-(5-methyl-2-pyridinyl)-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see intermediate 43) (34 mg, 0.065 mmol) in tetrahydrofuran (THF) (3 mL) was added TBAF (1M in THF, 0.085 mL, 0.085 mmol). The resulting mixture was stirred at room temperature for 30 min, and then was concentrated in vacuo. The residue was dissolved in a 1:1 (MeOH/DMSO) mixture (1 mL) and purified via MDAP (modifier: formic acid). The appropriate fractions were combined and concentrated under reduced pressure to give 2-(4-{(2S,4R)-1-acetyl-2-methyl-4-[(5-methyl-2-pyridinyl)amino]-1,2,3,4-tetrahydro-6-quinolinyl}-1H-1,2,3-triazol-1-yl)ethanol (19 mg, 0.045 mmol, 69%) as a colourless oil

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in a 1:1 (MeOH/DMSO) mixture (1 mL)
  3. custompurified via MDAP (modifier: formic acid)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0906e76960a4e60b14f0321aaaf6fa2
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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