Cesium fluoride → 5-[2-Benzyloxy-4-(6-benzyloxypyridin-2-ylmethyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660545

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=2)[CH:12]=[CH:11][C:10]=1[N:30]1[S:34](=[O:36])(=[O:35])[N:33](CC[Si](C)(C)C)[C:32](=[O:43])[CH2:31]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:17]=2)[CH:12]=[CH:11][C:10]=1[N:30]1[S:34](=[O:35])(=[O:36])[NH:33][C:32](=[O:43])[CH2:31]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-[2-benzyloxy-4-(6-benzyloxypyridin-2-ylmethyl)-phenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (213 mg, 0.35 mmol) in DMF (3 mL) is added CsF (265 mg, 1.75 mmol). The reaction is stirred at 60° C. for 2 h. The reaction is allowed to cool to RT and the solvent is removed under reduced pressure. The crude cesium salt of the title compound is used in the next step without further purification: (M+H)+=516.

Workup

temperatureto cool to RT
customthe solvent is removed under reduced pressure
customThe crude cesium salt of the title compound is used in the next step without further purification

Sources & evidence

ORD record: ord-df3f2f0f04754981acdef5cf890756c8
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084448B2

Linked notes

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