Cesium carbonate → HCID 57725955, compound

HRID 1922249Notes

Reaction equation

HRID 1922249 reaction equation
[CH3:1][NH:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:22]=[CH:21][C:14]3[N:15]=[C:16](S(C)=O)[S:17][C:13]=3[CH:12]=2)[CH:7]=[CH:6][N:5]=1.[C:24](=[O:27])([O-])[O-].[Cs+].[Cs+]>C1(CO)CCCCC1>[CH:11]1([CH2:24][O:27][C:16]2[S:17][C:13]3[CH:12]=[C:11]([O:10][C:8]4[CH:7]=[CH:6][N:5]=[C:4]([C:3]([NH:2][CH3:1])=[O:23])[CH:9]=4)[CH:22]=[CH:21][C:14]=3[N:15]=2)[CH2:22][CH2:21][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 577253932-Pyridinecarboxamide, N-methyl-4-[[2-(methylsulfinyl)-6-benzothiazolyl]oxy]-

Product 1

HCID 57725955HCID 57725955, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 7507CyclohexanemethanolSolvent

Conditions

Temperature
90 °C

Procedure

N-methyl-4-(2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)picolinamide (15 mg, 43 μmol) was mixed with 500 μL of cyclohexylmethanol and cesium carbonate (42 mg, 0.13 mmol). The resulting reaction mixture was stirred at 90° C. for 12 hours. The crude reaction mixture was filtered and purified on prep HPLC and then evaporated in vacuo to give 4-(2-(cyclohexylmethoxy)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide (7 mg, 17.6 μmol) as powder. ES/MS m/z 398.1 (MH+).

Workup

  1. customThe resulting reaction mixture
  2. customThe crude reaction mixture
  3. filtrationwas filtered
  4. custompurified on prep HPLC
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d0e3f55b151a417c99dd1cd2875c61fa
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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