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With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20.0℃; for 12.0h;
To a solution of the compound (1-E) (41.9 g, 123 mmol), 2-amino- 5-formylthiazole hydrochloride (30.4 g, 184 mmol) and N,N- EPO <DP n="70"/>dimethylaminopyridine (22.5 g, 184 mmol) in methylene chloride (1270 ml) was added dropwise N-ethyl-N'-(3-dimethylaminopropyl)- carbodiimide (28.6 g, 184 mmol) at room temperature. The mixture was stirred at the same temperature for 12 hours and concentrated in vacuo. The residue was purified by silica gel column chromatography (3% methanol-chloroform) to give the compound (1-F) (33.6 g, yield 61%) as pale yellow crystals. MS (m/z) APCI: 450 [M+H]+
(2) To a solution of the above compound (1-b) (64.5 g, 282 mmol) in methylene chloride (322 ml) was added dropwise trifluoroacetic acid (322 ml) under ice-cooling over 20 minutes. The reaction mixture was stirred at room temperature for 2 hours, and evaporated. To the residue was added chloroform (50 ml), and then thereto was added dropwise a solution of 4N hydrogen chloride in dioxane (300 ml) under ice-cooling. The mixture was evaporated, and then the residue was washed with ethyl acetate and dried to give the above compound (1-c) (41.3 g) as a monohydrochloride. MS(m/z)APCI: Not Determined.
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