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Methoxytrimethylsilane → 5-[2-Hydroxy-4-(1H-pyrrol-3-yl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660732
Notes
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Reaction equation

HRID 660732 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[CH:11][N:10]([Si](C(C)C)(C(C)C)C(C)C)[CH:9]=2)[CH:5]=[CH:4][C:3]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1.C1C=CN=CC=1.F.[Si](OC)(C)(C)C>CC#N>[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[CH:11][NH:10][CH:9]=2)[CH:5]=[CH:4][C:3]=1[N:23]1[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 15771MethoxytrimethylsilaneHCID 64774Pyridine, hydrofluoride (1:1)HCID 68838285HCID 68838285, compound

Product 1

HCID 577773805-[2-Hydroxy-4-(1H-pyrrol-3-yl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-[2-hydroxy-4-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one in MeCN (10 mL) is added HF-Pyridine (0.2 mL, 2.23 mmol) and the reaction mixture is stirred at RT for 2 h. TMSOMe (5 mL) is added to consume unreacted HF, and the crude reaction mixture is concentrated in vacuo. The residue is purified by reverse phase MPLC using 1-40% MeCN/H2O as eluent to give the title compound: (M−1)−=292.

Workup

  1. customto consume unreacted HF
  2. customthe crude reaction mixture
  3. concentrationis concentrated in vacuo
  4. customThe residue is purified by reverse phase MPLC

Sources & evidence

ORD record
ord-cf9de93ee3c3470bb763eb37b95e4aa7
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084448B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes