Home Cart Sign in  
Chemical Structure| 1525616-82-3 Chemical Structure| 1525616-82-3

Structure of 1525616-82-3

Chemical Structure| 1525616-82-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1525616-82-3 ]

CAS No. :1525616-82-3
Formula : C13H18BrN3O2
M.W : 328.20
SMILES Code : O=C(NCCN1CCOCC1)C2=CC(Br)=CC(N)=C2
MDL No. :MFCD25136614

Safety of [ 1525616-82-3 ]

Application In Synthesis of [ 1525616-82-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1525616-82-3 ]

[ 1525616-82-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2038-03-1 ]
  • [ 42237-85-4 ]
  • [ 1525616-82-3 ]
YieldReaction ConditionsOperation in experiment
92% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 0 - 20℃; for 19h; Intermediate D1 : 3-Amino-5-ethynyl-A -(2-morpholinoethyl)benzamide. To a suspension of T3P (2.76 mL, 4.63 mmol), <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (1.00 g, 4.63 mmol) and Et3N (1.9 mL, 14 mmol) in DCM (20 mL) at 0C was added 2-morpholino ethanamine (0.91 mL, 6.9 mmol) and the mixture allowed to warm to RT for 18 hr. Additional aliquots of T3P (2.76 mL, 4.63 mmol) and 2-morpholinoethanamine (0.91 mL, 6.9 mmol) were added and after 1 hr the resulting mixture was partitioned with sat. aq NaHC03 (20 mL). The aq layer was separated and was extracted with DCM (20 mL) and the combined organics layers were washed with brine and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02, 40 g, MeOH in DCM, 2-5%, gradient elution) to afford 3-amino-5-bromo-/V-(2-morpholinoethyl)benzamide as a yellow crystalline solid (1.4 g, 92%); Rl 0.16 min (Method 2 acidic); m/z 328/330 (M+H)+ (ES+). To a degassed suspension of the benzamide obtained above (500 mg, 1.52 mmol), copper(l) iodide (29.0 mg, 0.152 mmol), and ethynyltriisopropylsilane (0.51 mL, 2.3 mmol) in a mixture of Et3N (3.0 mL) and DMF (3.0 mL), was added Pd(PPh3)4 (176 mg, 0.152 mmol) and the mixture heated to 80C for 1 hr, and then cooled to RT. The solids were removed by filtration through celite and the volatiles evaporated in vacuo to provide a crude product which was purified by flash column chromatography (Si02,12 g, MeOH in DCM, 5-10%, gradient elution) to afford 3-amino-/V-(2-morpholinoethyl)-5-((triisopropylsilyl)ethynyl)benzamide as a pale yellow gum (600 mg, 92%); Rl 1.84 min (Method 2 acidic); m/z 430 (M+H)+ (ES+) To a solution of the alkynylsilane obtained above (500 mg, 1.164 mmol) in THF (5.0 mL) was added TBAF (116 mL, 1.16 mmol) and the mixture maintained at RT for 1h. An additional aliquot of TBAF (114 mu, 1.16 mmol) was added and after 30 min the reaction mixture was partitioned between water (10 mL) and ethyl acetate (10 mL). The organic layer was separated and was washed with brine and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (Si02,12 g, MeOH in DCM, 2-5%, gradient elution) to afford the title compound Intermediate D1 , as a colourless gum (260 mg, 82%); R' 1.17 min (Method 2 basic); LCMS m/z 274 (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 ofT3P (1-propanephosphonic acid cyclic anhydride) (2.76 mL, 4.63 mmol), <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (ig, 4.63 mmol) and TEA (1.936 mL, 13.89 mmol) in DCM (20m1)Allowed to warm to room temperature and stirred overnight. More T3P (2.76 mL, 4.63 mmcl) and 2-morpholinoethanamine (0.911 mL, 6.94 mmol) were added and stirred for a further lh. Partitioned with sat. NaHCO3 soin. (20m1), the aqueous layer separated and partitioned with fresh DCM (20m1). The organics separated, bulked and partitioned with 20%wlw NaCI soln. The organic layer was separated, dried (MgSO4) filtered and solventevaporated. The crude product was purified by chromatography on the Companion (40 gcolumn, 2% MeOH:DCM to 5%) to afford the sub-title compound (1.4g) as a yellowcrystalline solid.1H NMR (400 MHz, DMSO-d6) O 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 (Mi-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 (50Wt% in EtOAc, 56.2 mL, 94 mmol), was added carefully to a solution of 3-amino- 5-bromobenzoic acid (13.6 g, 63.0 mmol), 2-morpholinoethanamine (16.52 mL, 126 mmol) and TEA (26.3 mL, 189 mmol) in DCM (200 mL). Ice bath used sporadically to prevent temperature rising above 35C. Stirred at rt for 1 h then partitioned with sat. aq. NaHC03 soln. (250 mL). Aqueous separated and partitioned with fresh DCM (250 mL), organics separated, bulked and partitioned with 20%w/w NaCI soln. (250 mL). Organic layer was separated, dried (MgS04), filtered and solvent evaporated. The crude product was dissolved in DCM (100 mL) and the sub-title product (13 g) crystallised out on standing as a light tan crystalline solid. 1 H NMR (400 MHz, DMSO-d6) delta 8.29 (t, 1 H), 7.06 (t, 1 H), 6.98 (t, 1 H), 6.85 (t, 1 H), 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)+
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+)

 

Historical Records