Cesium carbonate → HCID 58577578, compound

HRID 410223Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]2([F:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:14][C:8]1([C:7]2[C:2]([O:31][C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:16]4[S:15][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[N:17]=4)=[CH:30][CH:29]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 90 °C

Procedure

To 2-chloro-3-(4-fluorotetrahydro-2H-pyran-4-yl)pyridine (0.11 g, 0.510 mmol) was added to 4-(benzo[d]thiazol-2-ylamino)phenol (0.124 g, 0.510 mmol) with cesium carbonate (0.332 g, 1.020 mmol) in DMSO (1 mL). The resulting mixture was heated to 90° C. overnight. Aqeuous work up and purification by prep-plate TLC (3% MeOH/DCM) produced desired product. MS (ESI, pos. ion) m/z: 422 (M+1). IC50 (uM) +++++.

Workup

customAqeuous work up and purification by prep-plate TLC (3% MeOH/DCM)

Sources & evidence

ORD record: ord-477c3cc7957e496ea9b859cdcbe93896
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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