Cesium carbonate → 1-(5,6-dichloro-2-methoxypyridin-3-yl)-N-(1,3,4-thiadiazol-2-yl)isoquinoline-6-sulfonamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([S:21]([O:24]C4C(F)=C(F)C(F)=C(F)C=4F)(=[O:23])=O)=[CH:18][CH:19]=3)[CH:14]=[CH:13][N:12]=2)[C:5]([O:9][CH3:10])=[N:6][C:7]=1[Cl:8].[S:36]1[CH:40]=[N:39][N:38]=[C:37]1[NH2:41].C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([S:21]([NH:41][C:37]4[S:36][CH:40]=[N:39][N:38]=4)(=[O:24])=[O:23])=[CH:18][CH:19]=3)[CH:14]=[CH:13][N:12]=2)[C:5]([O:9][CH3:10])=[N:6][C:7]=1[Cl:8]Participants
4
Procedure
A vial was charged with perfluorophenyl 1-(5,6-dichloro-2-methoxypyridin-3-yl)isoquinoline-6-sulfonate (0.042 g, 0.076 mmol), 1,3,4-thiadiazol-2-amine (8.48 mg, 0.084 mmol), and cesium carbonate (0.074 g, 0.229 mmol). The vial was flushed with Ar (g), then acetonitrile (0.381 ml) was added. The reaction was stirred for four hours at room temperature. The mixture was diluted with EtOAc and 1 N aq. HCl. The layers were separated, and the aq. layer was extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to afford crude 1-(5,6-dichloro-2-methoxypyridin-3-yl)-N-(1,3,4-thiadiazol-2-yl)isoquinoline-6-sulfonamide as a yellow solid. (ESI) 470.0 (M+H)+.
Workup
- customThe vial was flushed with Ar (g)
- additionacetonitrile (0.381 ml) was added
- additionThe mixture was diluted with EtOAc and 1 N aq. HCl
- customThe layers were separated
- extractionthe aq. layer was extracted with EtOAc (2×)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6c91f3a8b06148fcba047f36f4743dd9
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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