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

HRID 1880040Notes

Reaction equation

HRID 1880040 reaction equation
Cl[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[S:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[C:15]1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cl-].[Na+]>[O:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:2]([O:30][C:27]3[CH:26]=[CH:25][C:24]([NH:23][C:15]4[S:14][C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=5[N:16]=4)=[CH:29][CH:28]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 529403224-(2-Chloropyridin-3-yl)morpholineHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenol

Product 1

HCID 59327176N-(4-(3-morpholinopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 5234Sodium ChlorideSolvent

Procedure

To a round bottomed flask was added 4-(2-chloropyridin-3-yl)morpholine (0.2076 g, 1.045 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (0.304 g, 1.254 mmol), and cesium carbonate (0.409 g, 1.254 mmol) in DMSO (3.48 mL) at 80° C. for two days. The reaction was allowed to cool to room temperature. The reaction mixture was diluted with a 50% sodium chloride solution and extracted with DCM. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (25M), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide N-(4-(3-morpholinopyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine. MS (ESI, pos. ion) m/z: 405 (M+1). IC50 (uM) +++++.

Workup

  1. extractionextracted with DCM
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed through a Biotage pre-packed silica gel column (25M)
  8. washeluting with a gradient of 10% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-860a9190ae994929aece8397820aea63
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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