| 13 g |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20 - 35℃; for 3h; |
T3P (50% w/w in EtOAc, 56.2 mL, 94 mmol), was added carefully to a solution of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (13.6 g, 63.0 mmol), 2-morpholinoethanamine (16.52 mL, 126 mmol) and Et3N (26.3 mL, 189 mmol) in DCM (200 mL). An ice bath was used sporadically to prevent temperature rising above 35 C. Reaction stirred at room temperature for 1 h. Partitioned with sat. aq. NaHCO3 solution (250 mL). Aqueous separated and partitioned with fresh DCM (250 mL). Organics separated, bulked and partitioned with 20% w/w NaCl solution (250 mL). The organic layer was separated, dried (MgSO4), filtered and solvent evaporated. The crude product was dissolved in DCM (100 mL) and the sub-title compound (13 g) crystallised out on standing as a light tan crystalline solid. 1H NMR (400 MHz, DMSO-d6) delta 8.29 (t, 1H), 7.06 (t, 1H), 6.98 (t, 1H), 6.85 (t, 1H), 5.59 (s, 2H), 3.57 (t, 4H), 3.41-3.26 (m, 2H), 2.48-2.33 (m, 6H). LCMS m/z 328/330(M+H)+ (ES+) |
| 13 g |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20 - 35℃; for 1h; |
T3P (50% wlw in EtOAc, 56.2 mL, 94 mmol), was added carefully to a solution of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (13.6 g, 63.0 mmol), 2-morpholinoethanamine (16.52 mL, 126 mmol) andEt3N (26.3 mL, 189 mmol) in DCM (200 mL). An ice bath was used sporadically to preventtemperature rising above 35C. Reaction stirred at room temperature for lh. Partitionedwith sat. aq. NaHCO3 solution (250 mL). Aqueous separated and partitioned with fresh DCM (250 mL). Organics separated, bulked and partitioned with 20%wlw NaCI solution (250 mL). The organic layer was separated, dried (MgSO4), filtered and solvent evaporated. The crude product was dissolved in DCM (100 mL) and the sub-title compound (13 g) crystallised outon standing as a light tan crystalline solid.1H NMR (400 MHz, DMSO-d6) O 8.29 (t, 1H), 7.06 (t, 1H), 6.98 (t, 1H), 6.85 (t, 1H), 5.59 (5, 2H), 3.57 (t, 4H), 3.41 - 3.26 (m, 2H), 2.48 - 2.33 (m, 6H).LCMS mlz 328/330(M+H) (ES) |
| 13 g |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; ethyl acetate; at 20 - 35℃; for 1h; |
(i) 3-Ami no-5-bromo-N-(2-morphol inoethyl) benzam ideT3P (50% w/w in EtOAc, 56.2 ml, 94 mmcl), was added carefully to a solution of 3-amino-5-bromobenzcic acid (13.6 g, 63.0 mmcl), 2-mcrpholincethanamine (16.52 mL, 126 mmcl) andEt3N (26.3 mL, 189 mmol) in DCM (200 mL). An ice bath was used sporadically to prevent temperature rising above 35C. Reaction stirred at room temperature for I h. Partitioned with sat. eq. NaHCO3 solution (250 mL). Aqueous separated and partitioned with fresh DCM (250 mL). Organics separated, bulked and partitioned with 20%wlw NaCI solution (250 mL).The organic layer was separated, dried (MgSO4), filtered and solvent evaporated. The crude product was dissolved in DCM (100 mL) and the sub-title compound (13 g) crystallised cut on standing as a light tan crystalline solid.1H NMR (400 MHz, DMSO-d6) O 8.29 (t, IH), 7.06 (t, IH), 6.98 (t, IH), 6.85 (t, IH), 5.59 (s, 2H), 3.57 (t, 4H), 3.41 - 3.26 (m, 2H), 2.48 - 2.33 (m, 6H).LCMS m/z 328/330(M+H) (ES) |
| 1.4 g |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃;Cooling with ice; |
2-Morpholinoethanamine (0.911 mL, 6.94 mmol) was added to an ice cold suspension of T3P (2.76 mL, 4.63 mmol), <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (1 g, 4.63 mmol) and TEA (1.936 mL, 13.89 mmol) in DCM (20 mL). Allowed to warm to room temperature and stirred overnight. More T3P (2.76 mL, 4.63 mmol) and 2-morpholinoethanamine (0.911 mL, 6.94 mmol) were added and stirred for a further 1 h. Partitioned with saturated NaHCO3 solution (20 mL), the aqueous layer separated and partitioned with fresh DCM (20 mL). The organics separated, bulked and partitioned with 20% w/w NaCl solution. Organic layer separated, dried (MgSO4) filtered and solvent evaporated. The crude product was purified by chromatography on the Companion (40 g column, 2% MeOH:DCM to 5%) to afford the sub-title compound (1.4 g) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO) delta 8.28 (t, 1H), 7.06 (t, 1H), 6.98 (dd, 1H), 6.85 (t, 1H), 5.58 (s, 2H), 3.57 (t, 4H), 3.33 (m, 2H), 2.41 (m, 6H). LCMS m/z 328/330 (M+H)+ (ES+) |
| 1.4 g |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 1h; |
(i) 3-Amino-5-bromo-N-(2-morpholinoethyl)benzamide 2-Morpholinoethanamine (0.911 mL, 6.94 mmol) was added to an ice cold suspension of T3P (2.76 mL, 4.63 mmol), <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (1 g, 4.63 mmol) and TEA (1.936 mL, 13.89 mmol) in DCM (20 mL). Allowed to warm to room temperature and stirred overnight. More T3P (2.76 mL, 4.63 mmol) and 2-morpholinoethanamine (0.911 mL, 6.94 mmol) were added and stirred for a further 1 h. Partitioned with saturated NaHCO3 solution (20 mL), the aqueous layer separated and partitioned with fresh DCM (20 mL). The organics separated, bulked and partitioned with 20% w/w NaCl solution. Organic layer separated, dried (MgSO4) filtered and solvent evaporated. The crude product was purified by chromatography on the Companion (40 g column, 2% MeOH:DCM to 5%) to afford the sub-title compound (1.4 g) as a yellow crystalline solid. 1H NMR (400 MHz, DMSO) delta 8.28 (t, 1H), 7.06 (t, 1H), 6.98 (dd, 1H), 6.85 (t, 1H), 5.58 (s, 2H), 3.57 (t, 4H), 3.33 (m, 2H), 2.41 (m, 6H). LCMS m/z 328/330 (M+H)+ (ES+) |
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