Cesium carbonate → HCID 46208938, compound

HRID 887402Notes

Reaction equation

HRID 887402 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.[Cl:19][C:20]1[C:25](Cl)=[N:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[Cl:19][C:20]1[C:25]([O:16][C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:7]3[S:8][C:4]4[CH:3]=[C:2]([F:1])[CH:18]=[CH:17][C:5]=4[N:6]=3)=[CH:15][CH:14]=2)=[N:24][CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 785752,3-DichloropyrazineHCID 59351415HCID 59351415, compound

Product 1

HCID 46208938HCID 46208938, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(6-fluorobenzo[d]thiazol-2-ylamino)phenol (7.5 g, 0.028 mol) and 2,3-dichloropyrazine (5.0 g, 0.034 mol) in DMSO (35 mL) was added cesium carbonate (11.0 g, 0.034 mol). The mixture was heated to 80° C. for 2 h. The reaction mixture was cooled to RT and diluted with water (350 mL). The aqueous layer was extracted with EtOAc (4×300 mL). The combined organic extract was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography (silica 100-200 mesh; 30-60% ethyl acetate in hexane) to give N-(4-(3-chloropyrazin-2-yloxy)phenyl)-6-fluorobenzo[d]thiazol-2-amine as a white solid. [M+H]=372.8. IC50 (uM) +.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe aqueous layer was extracted with EtOAc (4×300 mL)
  3. extractionThe combined organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica 100-200 mesh; 30-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-88e2f29be34e4ab5858048ddcbee12ec
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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