Home Cart Sign in  
Chemical Structure| 565473-06-5 Chemical Structure| 565473-06-5

Structure of 565473-06-5

Chemical Structure| 565473-06-5

*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 [ 565473-06-5 ]

CAS No. :565473-06-5
Formula : C11H9BrN4
M.W : 277.12
SMILES Code : N#CC1=C(N)N(CC2=CC=CC=C2)C(Br)=N1

Safety of [ 565473-06-5 ]

Application In Synthesis of [ 565473-06-5 ]

* 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 [ 565473-06-5 ]

[ 565473-06-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 506-68-3 ]
  • [ 76513-69-4 ]
  • [ 89830-98-8 ]
  • [ 565473-06-5 ]
  • [ 1434584-96-9 ]
YieldReaction ConditionsOperation in experiment
120 mg J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0°C under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0°C. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H). BrCN (6.1 1 g; 57.7 mmol) was added to a solution of DMAP (7.05 g; 57.7 mmol) in DMF (60 mL) at 10°C. The reaction was exothermic to 35°C and a pale yellow precipitate was formed. The mixture was cooled to 10°C and J-1 b (5.5 g; 23.1 mmol) was added. The mixture was stirred at 40°C for 6 h. Water was added and product was extracted with Et20 (2 times). The combined organic layers were washed with brine, dried over MgS04, filtered and the solvent was removed under reduced pressure.The crude was purified by preparative LC (Irregular SiOH 15-40 ??? 220 g grace, mobile phase Heptane/DCM 50/50 to 10/90) to give 2.2 g impure J-1 , which was further purified by preparative LC (irregular SiOH 15-40 ??? 90 g Merck, mobile phase heptane/DCM 30/70) to give 0.94 g of J-1 as a mixture of two region-isomers(15percent yield).HPLC Rt (min) = 6.1 1 ; MS M+ (H+): 264 (method V1004V1012) EtONa (904 mg; 13.3 mmol) was added to a solution of 2-cyano-imidazole 1-1 (0.7 g; 2.66 mmol) and intermediate C-1 (736 mg; 2.66 mmol) in EtOH (30 ml_). The mixture was stirred at 90°C for 16 h. The solvent was removed under reduced pressure. The crude was purified by preparative LC (irregular SiOH 45g Merck, mobile phase 97/3/0.1 to 95/5/0.5) to give 0.51 g of the SEM-protected ethoxy intermediate as a lightly yellow solid (38percent yield).HPLC Rt (min) = 7.45 ; MS M+ (H+): 506 method (v2003v2002) NaF (170 mg; 4.05 mmol) was added to a solution of SEM-protected ethoxy intermediate (0.41 g; 0.81 1 mmol) in THF (28 ml_), HCI (37percent in H20) (28 mL) and MeOH (10 mL). The mixture was stirred at 40°C for 16h. The mixture was cooled to RT and a 10percent solution of K2C03 was added until the pH of the solution was basic. The aqueous layer was saturated with K2C03 powder and the product was extracted with DCM/MeOH (5percent) (3 times). The combined organic layers were dried over MgS04, filtered and the solvent was removed under reduced pressure. The crude was purified by preparative LC (irregular SiOH 15-40??"?, mobile phase DCM/MeOH/NH3aq 95/5/0.5 to 90/10/0.5) to give 120 mg of compound 1 as a white powder (43percent yield)
  • 2
  • [ 506-68-3 ]
  • [ 76513-69-4 ]
  • [ 89830-98-8 ]
  • [ 565473-06-5 ]
  • C24H31N7O2Si [ No CAS ]
  • C24H31N7O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
J-1 a (4.84 g; 44.8 mmol) in TH F (60 mL) was added dropwise to a suspension of NaH (1 .97 g; 49.2 mmol) in TH F (200 mL) at 0°C under N2. The mixture was stirred at RT for 30 min and SEM-CI (9.9 mL; 55.9 mmol) in THF(20 mL) was added dropwise at 0°C. The mixture was stirred at RT under N2 for 16 h. Water was added and the product was extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude was purified by preparative LC (Irregular SiOH 20-45 [Jim , 150g Merck, Mobile phase Gradient from 50percent DCM, 50percent heptane to 100percent DCM). The fractions containing pure compound were combined and the solvent was removed under reduced pressure to give 6.6 g of J-1 b as a yellow oil (62percent).Mixture of 2 regioisomers : 70/30Minoritory regioisomer : 1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.64 (s, 1 H), 6.56 (s, 1 H), 5.34 (s, 1 H), 3.45 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.52-0.57 (m, 2H), -0.04 (s, 9H).Majoritory regioisomer :1H NMR (DMSO-de, 400MHz) : 5(ppm) 7.56 (s, 1 H), 6.94 (s, 1 H), 5.20 (s, 1 H), 3.43 (t, J = 8.08 Hz, 2H), 1 .73-1 .78 (m, 1 H), 0.80-0.86 (m, 2H), 0.72-0.74 (m, 2H), 0.56-0.62 (m, 2H), -0.04 (s, 9H). BrCN (6.1 1 g; 57.7 mmol) was added to a solution of DMAP (7.05 g; 57.7 mmol) in DMF (60 mL) at 10°C. The reaction was exothermic to 35°C and a pale yellow precipitate was formed. The mixture was cooled to 10°C and J-1 b (5.5 g; 23.1 mmol) was added. The mixture was stirred at 40°C for 6 h. Water was added and product was extracted with Et20 (2 times). The combined organic layers were washed with brine, dried over MgS04, filtered and the solvent was removed under reduced pressure.The crude was purified by preparative LC (Irregular SiOH 15-40 ??? 220 g grace, mobile phase Heptane/DCM 50/50 to 10/90) to give 2.2 g impure J-1 , which was further purified by preparative LC (irregular SiOH 15-40 ??? 90 g Merck, mobile phase heptane/DCM 30/70) to give 0.94 g of J-1 as a mixture of two region-isomers(15percent yield).HPLC Rt (min) = 6.1 1 ; MS M+ (H+): 264 (method V1004V1012) EtONa (904 mg; 13.3 mmol) was added to a solution of 2-cyano-imidazole 1-1 (0.7 g; 2.66 mmol) and intermediate C-1 (736 mg; 2.66 mmol) in EtOH (30 ml_). The mixture was stirred at 90°C for 16 h. The solvent was removed under reduced pressure. The crude was purified by preparative LC (irregular SiOH 45g Merck, mobile phase 97/3/0.1 to 95/5/0.5) to give 0.51 g of the SEM-protected ethoxy intermediate as a lightly yellow solid (38percent yield).HPLC Rt (min) = 7.45 ; MS M+ (H+): 506 method (v2003v2002)
 

Historical Records

Technical Information

Categories