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HRID2178223

反应详情

EQUATION

反应方程式

HRID 2178223 的结构方程式

REACTANTS

反应物

3
结构：CO
HCID887

Methanol

CH4O

结构：[K+].[OH-]
HCID14797

Potassium hydroxide

HKO

结构：CCOC(=O)c1nc(-c2ccc3c(c2)N(C(=O)Nc2nc4ccccc4s2)CCO3)sc1N(C)CCOc1ccccc1
HCID59418665

未命名化合物

PRODUCTS

生成物

1
结构：CN(CCOc1ccccc1)c1sc(-c2ccc3c(c2)N(C(=O)Nc2nc4ccccc4s2)CCO3)nc1C(=O)O
HCID46840789

未命名化合物

收率 8%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：O
溶剂HCID962

Water

H2O

CONDITIONS

反应条件

温度
55 °C

PROCEDURE

实验过程

The title compound 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acid (20) was prepared by the following procedure: To ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20C) (0.210 g, 0.34 mmol) and KOH (0.1 g, 1.8 mmol) was added MeOH (2 mL) and water (5 mL). The reaction mixture was allowed to heat to 55° C. and stirred 24 hours. The reaction was monitored by LCMS. To the reaction mixture was added (0.1 g, 1.8 mmol). The reaction mixture was allowed to heat to 55° C. and stirred for 24 hours. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the crude residue was added EtOAc and water. The layers were separated and extracted with EtOAc and the combined organic extracts were washed sequentially with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse phase HPLC to provide 0.015 g (8%) of the desired product 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acid (20): LC/MS (APCI): m/z 588.1 (M+H).

WORKUP

后处理

  1. customThe title compound 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acid (20) was prepared by the following procedure
  2. additionTo the reaction mixture was added (0.1 g, 1.8 mmol)
  3. temperatureto heat to 55° C.
  4. stirringstirred for 24 hours
  5. temperatureThe reaction mixture was cooled to rt
  6. concentrationconcentrated under reduced pressure
  7. additionTo the crude residue was added EtOAc and water
  8. customThe layers were separated
  9. extractionextracted with EtOAc
  10. washthe combined organic extracts were washed sequentially with water, brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe crude residue was purified by reverse phase HPLC