Cesium carbonate → HCID 58965035, compound

HRID 913371Notes

Reaction equation

HRID 913371 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:15][CH3:16])[S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:17])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]1[S:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1>CN(C)C=O>[S:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[CH2:25][O:17][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[S:14][C:13]([CH2:15][CH3:16])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 1363391164-Amino-2-ethylthiazolo[4,5-c]quinolin-7-ol

Product 1

HCID 58965035HCID 58965035, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Conditions

Temperature
60 °C

Procedure

A scintillation vial was charged with 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol and anhydrous N,N-dimethylformamide (DMF, 2 mL). The mixture was warmed until a solution was obtained. An additional amount of DMF (1 mL) was added. To this stirred orange solution was added cesium carbonate (3.0 eq.) and a solution of 2-(bromomethyl)benzothiazole dissolved in DMF (2 mL). Additional DMF (1 mL) was used to rinse the vial. The vial was capped and heated to 60° C. overnight. The reaction was monitored by HPLC. The reaction was quenched by adding the reaction mixture dropwise to water (60 mL) with stirring. A precipitate formed. The solid was collected by vacuum filtration. The solid was then dissolved in methanol and adsorbed onto silica gel (6 g) for purification by HPFC (0-15% CMA in chloroform, 1440 mL). Pure fractions were combined and concentrated; the resulting solid was recrystallized from acetonitrile to provide 7-[(1,3-benzothiazol-2-yl)methoxy]-2-ethylthiazolo[4,5-c]quinolin-4-amine as a white crystalline solid, mp. 211-212° C. MS (APCI) m/z 393 (M+H)+. Anal. calcd C20H16N4OS2.0.6H2O: C, 59.56; H, 4.30; N, 13.89. Found: C, 59.66; H, 4.08; N, 13.80.

Workup

  1. temperatureThe mixture was warmed until a solution
  2. customwas obtained
  3. washto rinse the vial
  4. customThe vial was capped
  5. customThe reaction was quenched
  6. additionby adding the reaction mixture dropwise to water (60 mL)
  7. customA precipitate formed
  8. filtrationThe solid was collected by vacuum filtration
  9. dissolutionThe solid was then dissolved in methanol
  10. customadsorbed onto silica gel (6 g) for purification by HPFC (0-15% CMA in chloroform, 1440 mL)
  11. concentrationconcentrated
  12. customthe resulting solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-6c59a07768464c41a0dbd759fd656dfa
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

Loading…