Cesium carbonate → HCID 57725444, compound

HRID 2370580Notes

Reaction equation

[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:7]1)(=[O:5])=[O:4])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:29][C:30]1[CH:35]=[C:34](F)[CH:33]=[CH:32][N:31]=1>CN1C(=O)CCC1.O.C(OCC)(=O)C>[Cl:29][C:30]1[CH:35]=[C:34]([O:22][C:20]2[CH:19]=[CH:18][C:16]3[N:17]=[C:13]([NH:12][C@H:8]4[CH2:9][CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:7]4)[S:14][C:15]=3[CH:21]=2)[CH:33]=[CH:32][N:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of (S)-2-(1-(ethylsulfonyl)piperidin-3-ylamino)benzo[d]thiazol-6-ol (1.15 g, 3.37 mmol) and cesium carbonate (2.20 g, 6.74 mmole) in 12 ml of NMP was added 2-chloro-4-fluoropyridine (532 mg, 4.05 mmol). The reaction mixture was stirred at 60° C. for 17 hours. The reaction mixture was diluted with water (100 ml) and ethyl acetate (100 ml). The separated organic layer was washed with water (3×50 ml), saturated sodium bicarbonate solution (3×50 ml), water (50 ml), brine (100 ml) and dried over sodium sulfate. Concentration in vacuo and purification by flash chromatography over silica gel with ethyl acetate:hexane (1:1 to 3:1) provided the title compound. Yield: 671 mg. ES/MS m/z 453.0 (MH), Rt=2.59 min.

Workup

washThe separated organic layer was washed with water (3×50 ml), saturated sodium bicarbonate solution (3×50 ml), water (50 ml), brine (100 ml)
dry with materialdried over sodium sulfate
concentrationConcentration
customin vacuo and purification by flash chromatography over silica gel with ethyl acetate:hexane (1:1 to 3:1)

Sources & evidence

ORD record: ord-8f51df92d8904515a1df36ee11709304
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710048B2

Reaction notes

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