Cesium fluoride → 5-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660493Notes

Reaction equation

HRID 660493 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]2[N:18]([CH2:22][O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N:31]1[S:35](=[O:37])(=[O:36])[N:34](CC[Si](C)(C)C)[C:33](=[O:44])[CH2:32]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](/[CH:15]=[CH:16]/[C:17]2[N:18]([CH2:22][O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:44])[CH2:32]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 688431025-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Product 1

HCID 689170015-{2-Benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl} 1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-{2-benzyloxy-4-[(E)-2-(2-benzyloxymethyl-2H-pyrazol-3-yl)-vinyl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (330 mg, 0.50 mmol)) and CsF (400 mg, 2.6 mmol) in DMF (5 mL) is heated at 60° C. for 18 h. The mixture is partitioned between aqueous NH4Cl and EtOAc and the organic layer is concentrated to afford the title compound which is used directly in the next step: (M+1)+=531.

Workup

  1. customThe mixture is partitioned between aqueous NH4Cl and EtOAc
  2. concentrationthe organic layer is concentrated

Sources & evidence

ORD record
ord-7fd3a1f2901e45f9868010bef08c0622
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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