Methanol → HCID 58965020, compound

HRID 913374Notes

Reaction equation

HRID 913374 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][CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1.CO>CN(C=O)C>[CH2:15]([C:13]1[S:14][C:10]2[C:9]3[CH:8]=[CH:7][C:6]([O:17][CH2:25][CH2:26][C:27]4[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[NH:29][CH:28]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 769243-(2-Bromoethyl)indoleHCID 1363391164-Amino-2-ethylthiazolo[4,5-c]quinolin-7-ol

Product 1

HCID 58965020HCID 58965020, 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 (1.0 eq., 1.0 mmol) and anhydrous 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., 3.0 mmol) and a solution of 3-(2-bromoethyl)indole (1.0 eq., 1.0 mmol) 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 drop-wise 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 methanol to provide a peach colored crystalline solid, mp 218-220° C. MS (APCI) m/z 389 (M+H)+. Anal. calcd for C22H20N4OS.0.8 CH3OH: C, 66.13; H, 5.65; N, 13.53. Found: C, 66.43; H, 5.03; N, 13.90.

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 drop-wise 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 methanol
  13. customto provide a peach colored crystalline solid, mp 218-220° C

Sources & evidence

ORD record
ord-d8eda18189e14ab6aa9884dda324a3be
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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