Cesium carbonate → HCID 67393198, compound

HRID 913372Notes

Reaction equation

HRID 913372 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+].Cl[CH2:25][C:26]1[O:30][C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][CH:27]=1>CN(C=O)C>[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]([O:17][CH2:25][C:26]3[O:30][C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][CH:27]=3)=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylateHCID 1363391164-Amino-2-ethylthiazolo[4,5-c]quinolin-7-ol

Product 1

HCID 67393198HCID 67393198, 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 ethyl 5-(chloromethyl)-2-furancarboxylate (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. Crude ethyl 5-{[(4-amino-2-ethylthiazolo[4,5-c]quinolin-7-yl)oxy]methyl}-2-furoate was isolated as a solid 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 to provide a solid which analysis indicated was the methyl ester. This material was recrystallized from acetonitrile to provide methyl 5-{[(4-amino-2-ethylthiazolo[4,5-c]quinolin-7-yl)oxy]methyl}-2-furoate as a light yellow crystalline solid, mp 184-186° C. MS (APCI) m/z 384 (M+H)+. Anal. calcd for C19H17N3O4S.0.30CH3CN: C, 59.49; H, 4.56; N, 11.68. Found: C, 59.35; H, 4.22; N, 11.71.

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

Sources & evidence

ORD record
ord-dd5f8297f9444c5ebc972d7b9d85ba78
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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