Tetrabutylammonium Fluoride → HCID 58456204, compound

HRID 410504Notes

Reaction equation

HRID 410504 reaction equation
CC(C)([Si](C)(C)[O:5][CH2:6][CH2:7][C:8]([C:20]1[S:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]3[N:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][N:33]=3)[CH:26]=2)=[CH:23][N:24]=1)([OH:19])[CH2:9][CH2:10][O:11][Si](C)(C)C(C)(C)C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:41][C:38]([F:39])([F:40])[C:36]1[CH:35]=[CH:34][N:33]=[C:32]([NH:31][C:27]2[CH:26]=[C:25]([C:22]3[S:21][C:20]([C:8]([OH:19])([CH2:9][CH2:10][OH:11])[CH2:7][CH2:6][OH:5])=[N:24][CH:23]=3)[CH:30]=[CH:29][CH:28]=2)[N:37]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70925996HCID 70925996, compound

Product 1

HCID 58456204HCID 58456204, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 2 (196 mg, 0.293 mmol) in THF (3 mL) was added TBAF (1 M in THF, 1.465 mL, 1.465 mmol) and the solution was stirred overnight at room temperature. Solvent was removed by evaporation and the residue was purified by flash chromatography to give 3-[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]pentane-1,3,5-triol (79.8 mg, 0.181 mmol, 61.8% yield) as an off-white fluffy solid. APCI: [M+H]+ m/z 441.1. 1H NMR (500 MHz, acetone-d6): δ 9.30 (1H, s), 8.86 (1H, d, J=4.89 Hz), 8.34-8.32 (1H, m), 8.06 (1H, s), 7.84-7.79 (1H, m), 7.47-7.41 (1H, m), 7.39 (1H, dt, J=7.76, 1.40 Hz), 7.27 (1H, d, J=4.88 Hz), 6.00 (1H, s), 4.04 (2H, t, J=4.74 Hz), 3.77-3.68 (4H, m), 2.25-2.19 (4H, m). rhSYK activity=++

Workup

  1. customSolvent was removed by evaporation
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-549883cb661f44daa1968e6e1ff7429f
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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