Cesium carbonate → HCID 59485627, compound

HRID 1972268Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][NH:15][C:14]3=[O:28])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:38]1[CH:43]=[N:42][CH:41]=[CH:40][N:39]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=4)[CH2:16][N:15]([C:38]4[CH:43]=[N:42][CH:41]=[CH:40][N:39]=4)[C:14]3=[O:28])=[CH:11][CH:12]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (S)-1-(4-(4-chlorophenoxy)phenyl)-5-(3-(trifluoromethyl)phenyl)imidazolidin-2-one (20.0 mg, 0.046 mmol) in DMF (0.5 mL) are added Cs2CO3 (30.1 mg, 0.092 mmol) and chloropyrazine (8.25 μL, 0.092 mmol). The reaction mixture is heated at 100° C. overnight, and additional Cs2CO3 (30.1 mg, 0.092 mmol) and chloropyrazine (8.25 μL, 0.092 mmol) are added. After heating at 100° C. for another 8 h, the reaction mixture is quenched with H2O (5 mL) and extracted with EtOAc (3×3 mL). The combined organic layer is evaporated under vacuo and purified by preparatory LC/MS to provide the title compound; HPLC-MS calculated for C26H18ClF3N4O2 (M+H+) 511.1, found 511.1.

Workup

temperatureAfter heating at 100° C. for another 8 h
customthe reaction mixture is quenched with H2O (5 mL)
extractionextracted with EtOAc (3×3 mL)
customThe combined organic layer is evaporated under vacuo
custompurified by preparatory LC/MS

Sources & evidence

ORD record: ord-e80cf3ca287b41a78eaf513eba3a1f4b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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