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

HRID 1642614Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[C:20]([CH2:22][CH3:23])[CH:19]=[CH:18][N:17]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[S:28](=[O:30])(=[O:29])[N:27](CC[Si](C)(C)C)[C:26](=[O:37])[CH2:25]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]=[C:20]([CH2:22][CH3:23])[CH:19]=[CH:18][N:17]=2)[CH:12]=[CH:11][C:10]=1[N:24]1[S:28](=[O:30])(=[O:29])[NH:27][C:26](=[O:37])[CH2:25]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-(4-ethylpyridin-2-ylmethyl) -phenyl]-1,1-dioxo-2-(2-trimethylsilanyl-ethyl)-1,2,5-thiadiazolidin-3-one (47 mg, 0.088 mmol) in DMF (1 mL) is added CsF (80 mg, 0.53 mmol). The reaction is stirred at 60° C. for 2 h. The reaction is allowed to cool to ambient temperature and the solvent is evaporated under a stream of N2. The crude residue is taken up in acetonitrile and filtered, washing with acetonitrile several times. The solvent is removed under reduced pressure and the crude cesium salt of 5-[2-benzyloxy-4-(6-benzyloxypyridin-2-ylmethyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one is used in the next step without further purification: MS (M+H)+=516.

Workup

temperatureto cool to ambient temperature
customthe solvent is evaporated under a stream of N2
filtrationfiltered
washwashing with acetonitrile several times
customThe solvent is removed under reduced pressure
customthe crude cesium salt of 5-[2-benzyloxy-4-(6-benzyloxypyridin-2-ylmethyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one is used in the next step without further purification

Sources & evidence

ORD record: ord-4834e24d3d024b29a8f71f4361bfccff
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119666B2

Reaction notes

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