2,4-dichlorobenzohydrazide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of compound 8 (370 mg, 0.934 mmol) in 5 ml of CH2 Cl2 was added DIPEA (180 mg, 1.4 mmol) at 0° C. and stirred for 10 minutes. Then chloroacetyl chloride (116 mg, 1.02 mmol) was added slowly at the same temperature and the mixture was warmed to ambient temperature and stirred overnight. Solvent was removed to give the crude compound which was used in the next step without any further purification. The crude compound was heated to reflux in toluene (25 ml) using Dean-Stark for 12 hours. Then the toluene was distilled and the crude material purified by column chromatography using EtOAc:Hexane (45:55) as an eluent to afford compound 9 as a pale yellow gummy material (212 mg). Yield: 50%. stirred overnight Solvent was removed to give the crude compound which was used in the next step without any further purification The crude compound was heated to reflux in toluene (25 ml) for 12 hours Then the toluene was distilled the crude material purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared in analogy to Preparation 11 in 0.16 g yield starting from 2,4-dichlorobenzohydrazide (0.62 g) and N,N′-dimethyl-5-hexenimidamide hydrochloride (0.48 g). MS (m/z): 296 [MH]+. yield

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of compound 8 (370 mg, 0.934 mmol) in 5 ml of CH2 Cl2 was added DIPEA (180 mg, 1.4 mmol) at 0° C. and stirred for 10 minutes. Then chloroacetyl chloride (116 mg, 1.02 mmol) was added slowly at the same temperature and the mixture was warmed to ambient temperature and stirred overnight. Solvent was removed to give the crude compound which was used in the next step without any further purification. The crude compound was heated to reflux in toluene (25 ml) using Dean-Stark for 12 hours. Then the toluene was distilled and the crude material purified by column chromatography using EtOAc:Hexane (45:55) as an eluent to afford compound 9 as a pale yellow gummy material (212 mg). Yield: 50%. stirred overnight Solvent was removed to give the crude compound which was used in the next step without any further purification The crude compound was heated to reflux in toluene (25 ml) for 12 hours Then the toluene was distilled the crude material purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared in analogy to Preparation 11 in 0.16 g yield starting from 2,4-dichlorobenzohydrazide (0.62 g) and N,N′-dimethyl-5-hexenimidamide hydrochloride (0.48 g). MS (m/z): 296 [MH]+. yield

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of compound 8 (370 mg, 0.934 mmol) in 5 ml of CH2 Cl2 was added DIPEA (180 mg, 1.4 mmol) at 0° C. and stirred for 10 minutes. Then chloroacetyl chloride (116 mg, 1.02 mmol) was added slowly at the same temperature and the mixture was warmed to ambient temperature and stirred overnight. Solvent was removed to give the crude compound which was used in the next step without any further purification. The crude compound was heated to reflux in toluene (25 ml) using Dean-Stark for 12 hours. Then the toluene was distilled and the crude material purified by column chromatography using EtOAc:Hexane (45:55) as an eluent to afford compound 9 as a pale yellow gummy material (212 mg). Yield: 50%. stirred overnight Solvent was removed to give the crude compound which was used in the next step without any further purification The crude compound was heated to reflux in toluene (25 ml) for 12 hours Then the toluene was distilled the crude material purified by column chromatography