Water → 4-(2-(4-(Benzo[D]thiazol-2-ylamino)phenoxy)pyridin-3-YL)tetrahydro-2H-pyran-4-OL

HRID 1880092Notes

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.F[C:19]1[C:24]([C:25]2([OH:31])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O.[Cl-].[Na+].O>[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]([O:17][C:19]2[C:24]([C:25]3([OH:31])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-(benzo[d]thiazol-2-ylamino)phenol (0.123 g, 0.507 mmol) and 4-(2-fluoropyridin-3-yl)tetrahydro-2H-pyran-4-ol (0.1 g, 0.507 mmol) in DMSO (1 mL) was added cesium carbonate (0.330 g, 1.014 mmol). The resulting mixture was heated to 100° C. and stirred overnight. Aqueous work up with multiple water and brine washes to remove DMSO and extraction with DCM. Purification by Biotage (0-10% MeOH/DCM) produced product. MS (ESI, pos. ion) m/z: 420 (M+1). IC50 (uM) +++++.

Workup

customto remove
extractionDMSO and extraction with DCM
customPurification by Biotage (0-10% MeOH/DCM)
customproduced product

Sources & evidence

ORD record: ord-499a6fdefd3d4df0b270c061fd3ae215
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318718B2

Reaction notes

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