3-(chloromethyl)-N,N-dimethylbenzamide

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46-7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2.0.2H2O: C, 49.38; H, 4.28, N, 28.79. Found: C, 49.25; H, 4.09; N, 28.47. extracted with EtOAc dried (MgSO4) concentrated in vacuo

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

実験手順: A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46-7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2.0.2H2O: C, 49.38; H, 4.28; N, 28.79. Found: C, 49.25; H, 4.09; N, 28.47. extracted with EtOAc dried (MgSO4) concentrated in vacuo

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

実験手順: A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46–7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2. 0.2H2O: C, 49.38; H, 4.28, N, 28.79.Found: C, 49.25; H, 4.09; N, 28.47. extracted with EtOAc dried (MgSO4) concentrated in vacuo

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

実験手順: A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46–7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2. 0.2H2O: C, 49.38; H, 4.28, N, 28.79.Found: C, 49.25; H, 4.09; N, 28.47. extracted with EtOAc dried (MgSO4) concentrated in vacuo

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

実験手順: To a flask was added 3-iodo-4-nitro-1H-indazole (0.500 g, 1.73 mmol) and CH3CN (6 mL) followed by 2-tert-butyl-1,1,3,3-tetramethylguanidine (0.523 ml, 2.59 mmol). The mixture was stirred for 5 minutes, and then 3-(chloromethyl)-N,N-dimethylbenzamide (0.479 g, 2.42 mmol) was added as a CH3CN (4 mL) solution. The reaction was stirred at ambient temperature for 5 hours. The mixture was concentrated and diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (60 mL). The layers were mixed and separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (EtOAc) to provide 0.567 g (72%) of the desired product as an orange foam. The reaction was stirred at ambient temperature for 5 hours The mixture was concentrated diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (60 mL) The layers were mixed separated the organic phase was washed with brine dried over Na2SO4 filtered concentrated The crude product was purified by column chromatography (EtOAc)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of dimethylamine (2.91 mL, 5.82 mmol, 2.0M THF), NEt3 (0.885 mL, 6.35 mmol) and CH2Cl2 30 mL was cooled to 0° C. 3-(Chloromethyl)benzoyl chloride (1.0 g, 5.29 mmol) was added as a CH2Cl2 solution (3 mL) and the solution was stirred at 0° C. for 2 hours and then at ambient temperature for 2 hours. The reaction was washed with 1N HCl followed by brine, and the organic layer was dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (EtOAc) to provide 0.745 g (71%) of the product as colorless oil. at ambient temperature for 2 hours The reaction was washed with 1N HCl the organic layer was dried over Na2SO4 filtered concentrated The product was purified by column chromatography (EtOAc)

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

実験手順: The title compound is prepared in a manner substantially analogous to Procedure C using (4-Hydroxy-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone and 3-chloromethyl-N,N-dimethyl-benzamide [CAS 442910-26-1]. MS (ES+) 436.3

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

実験手順: The title compound is prepared in a manner substantially analogous to Procedure C using (4-Hydroxy-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone and 3-chloromethyl-N,N-dimethyl-benzamide [CAS 442910-26-1]. MS (ES+) 436.3

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46-7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2.0.2H2O: C, 49.38; H, 4.28, N, 28.79. Found: C, 49.25; H, 4.09; N, 28.47. extracted with EtOAc dried (MgSO4) concentrated in vacuo

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

実験手順: A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46-7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2.0.2H2O: C, 49.38; H, 4.28; N, 28.79. Found: C, 49.25; H, 4.09; N, 28.47. extracted with EtOAc dried (MgSO4) concentrated in vacuo