Cesium carbonate → N-(4-(3-chloropyrazin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

HRID 887389Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[Cl:18][C:19]1[C:24](Cl)=[N:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O.[Cl-].[Na+].O>[Cl:18][C:19]1[C:24]([O:17][C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[CH:12][CH:13]=2)=[N:23][CH:22]=[CH:21][N:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(benzo[d]thiazol-2-ylamino)phenol (3.1 g, 12.8 mmol) and 2,3-dichloropyrazine (2.29 g, 15.4 mmol) in DMSO (35 mL) was added cesium carbonate (5.0 g, 15.4 mmol). The reaction mixture was heated to 80° C. for 2 h. The mixture was cooled to RT, diluted with EtOAc and brine. The aqueous layer was extracted with EtOAc (2×) and the combined organics were dried over Na2SO4, filtered and concentrated. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 100% EtOAc in hexane, to provide N-(4-(3-chloropyrazin-2-yloxy)phenyl)benzo[d]thiazol-2-amine as light-tan solid.

Workup

temperatureThe mixture was cooled to RT
extractionThe aqueous layer was extracted with EtOAc (2×)
dry with materialthe combined organics were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (120 g)
washeluting with a gradient of 0% to 100% EtOAc in hexane

Sources & evidence

ORD record: ord-ba0819be21a6427c9bf209056b73ef56
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247418B2

Reaction notes

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