Structure of 953421-74-4
*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4.5
*For Research Use Only! Not for Human Use. We Do Not Sell to Patients.
Change View
| Size | Price | VIP Price |
DE Stock US Stock |
Asia Stock Global Stock |
In Stock |
| {[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.p_spot_brand_remark ]} 1-2 weeks {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock Inquiry - | Login - + |
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ item.p_spot_brand_remark ]}
1-2weeks
Inquiry
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
Asia Stock: Ship in 3-5 business days
EU Stock: ship in 0-1 business day
Global Stock: ship in 7-10 days
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
| CAS No. : | 953421-74-4 |
| Formula : | C9H4BrCl2N |
| M.W : | 276.94 |
| SMILES Code : | ClC1=CC2=C(C=C1)C(Br)=CN=C2Cl |
| English Name : | 4-Bromo-1,7-dichloroisoquinoline |
| MDL No. : | MFCD20528290 |
* 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.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 4-bromo-7-chloroisoquinoline 2-oxide With trichlorophosphate In chloroform at 66℃; for 3h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In chloroform; water; ethyl acetate | 3 4-bromo-7-chloroisoquinoline 2-oxide (3-7) (1.2 g, 4.64 mmol, 1.0 equiv.) was dissolved in anhydrous CHCl3 (20 mL) and treated dropwise with phosphorus oxychloride (0.649 mL, 6.96 mmol, 1.5 equiv.). The reaction mixture was refluxed at 66° C. LCMS after 3 hours showed only product. The reaction mixture was diluted with ethyl acetate, washed with saturated NaHCO3, and the organic layer was dried over Na2SO4, filtered and concentrated. The residue was triturated with hexane, and filtered to afford the product 3-8. LRMS m/z (M+H) 277.9 found, 277.9 required. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | Stage #1: 4-bromo-1,7-dichloroisoquinoline With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78 - -65℃; for 0.75h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; hexane at -60 - 20℃; for 1.16667h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 0℃; | 1001.4 Step 4To a slurry of solution of the product of Step 3, Example 1001, 4-bromo-l,7- dichloroisoquinoline (22.16 g, 80 mmol) in THF (500 ml) maintained at -78 °C was added 1.6 M n-BuLi in hexanes (100 mL, 160 mmol) drop wise via cannula over 15 min (the internal temperature was maintained <-65 °C). The solution was stirred for 0.5 h, and (i-PrO)3B (37 ml, 160 mmol) added drop wise via syringe over 10 min (the internal temperature was maintained <-65 °C). The reaction mixture was stirred for 0.5 h and 30% H2O2 (80 ml, 776 mmol) added dropwise via an addition funnel over 10 min (the internal temperature rose to -60 °C during this addition), followed by addition of IN NaOH solution (80 ml, 80 mmol). The cooling bath was removed and the reaction mixture allowed to warm to room temperature and stirred for an additional 1 h. After confirming the completion of the reaction by LC/MS, the reaction mixture was cooled to -40 °C, and a solution of 100 g of Na2S03 (0.793 moles) in 400 mL of ¾0 added dropwise over 30 min (the internal temperature was maintained between 5-10°C). The resulting slurry was neutralized with 6 N HC1 (approximately 50 ml) at 0 °C to provide a pH ~ 6. The mixture was diluted with 500 ml of EtOAc and decanted into a 2 L separatory funnel. To the remaining solid in the reaction vessel was added 500 mL of H20 and 300 ml of EtOAc and the mixture neutralized with 6 N HC1 (approximately 20 ml). The organic layers were combined in a separatory funnel, washed with brine (300 ml x 3) and ¾0 (200 ml x 3). The organic phase was dried over MgS04, filtered to remove the drying agent, and concentrated to give a crude product which was triturated with 50 ml of EtOAc. The resulting solid was collected by filtration, rinsed with EtOAc (3 x 25 ml) and dried to provide l,7-dichloroisoquinolin-4-ol (2 runs: 12.0 g, 70% and 13.8 g, 81%). The filtrates were combined, concentrated and purified by Biotage (35% EtOAc in hexanes) to give an additional 2.1 g of BMS-796007. In total, 27.9 g (82%) of 1,7- dichloroisoquinolin-4-ol was obtained. XH NMR (400 MHz, CD3OD) δ ppm 4.05 (s, 3 H), 7.4 (s, 1 H), 7.76 (dd, J=8.8, 2, Hz, 1 H), 8.16 (d, J=2 Hz, 1 H), 8.23 (d, J=8.8 Hz, 1 H); 13C MR (101 MHz, DMSO-D6) δ ppm 123.78, 124.66, 125.62, 127.03, 127.71, 130.72, 133.80, 137.63; 148.88; LC/MS, MS (m/z) (M+H)+ 213. |
| 82% | Stage #1: 4-bromo-1,7-dichloroisoquinoline With n-butyllithium In tetrahydrofuran; hexane at 65℃; for 0.75h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at 65℃; for 0.75h; Inert atmosphere; Stage #3: With dihydrogen peroxide; sodium sulfite In tetrahydrofuran; hexane; water at -60 - -40℃; for 0.5h; | |
| 81% | Stage #1: 4-bromo-1,7-dichloroisoquinoline With n-butyllithium In tetrahydrofuran; hexanes at -78 - -65℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexanes at -65℃; Stage #3: With dihydrogen peroxide In tetrahydrofuran; hexanes at -60℃; for 0.166667h; | 6.1.7 To a slurry of the product of Step 6 (22.16 g, 80 mmol) in THE (500 mL) at -78° C. was added 100 mL of 1.6 M n-BuLi (in hexanes, 160 mmol) dropwise via cannula over 15 min (maintaining the internal temperature <-65° C.). The resulting solution was stirred for 0.5 h, after such time, (i-PrO)3B (37 mL, 160 mmol) was added dropwise via syringe over 10 min (maintaining the internal temperature <-65° C.). The resulting reaction mixture was stirred for 0.5 h. After checking the reaction by LC/MS for completion, 80 ml of 30% H2O2 (776 mmol) was added dropwise via addition funnel over 10 min (the internal temperature rose to -60° C. during addition), followed by addition of 80 mL of 1 N NaOH (80 mmol). The cooling bath was removed, and the reaction mixture was allowed to warm to room temperature and stirred at room temperature for additional 1 h. After confirming the completion of the reaction by LC/MS, the reaction mixture was then cooled to -40° C., and a solution of 100 g of Na2SO3 (0.793 mole) in 400 mL of water was added dropwise via addition funnel as a means to quench excess H2O2 over 30 min (maintaining the internal temperature 5-10° C.). The resulting slurry was then neutralized with 6 N HCl (approximately 50 mL) at 0° C. till pH 6, then diluted with 500 mL of EtOAc and decanted to a 2 L separatory funnel. To the remaining solid in the reaction vessel was added 500 mL of water and 300 mL of EtOAc, then neutralized with 6 N HCl (approximately 20 mL). The combined organic layers were washed with brine (3×300 mL), then water (3×200 mL), dried over MgSO4, filtered, and concentrated to give a crude product which was triturated with 50 mL of EtOAc. The solid was collected by filtration, rinsed with EtOAc (3×25 mL) and dried to give desired product (2 runs: 12.0 g, 70% and 13.8 g, 81%). The filtrates were combined, concentrated and purified by flash column chromatography (SiO2, eluted with 35% EtOAc in hexanes to give 2.1 g of product. Overall, 44.4 g of bromide gave 27.9 g (81%) of 4-OH product. 1H NMR (400 MHz, CD3OD) δ ppm 4.05 (s, 3H), 7.4 (s, 1H), 7.76 (dd, J=8.8, 2, Hz, 1H), 8.16 (d, J=2 Hz, 1H), 8.23 (d, J=8.8 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ ppm 123.78, 124.66, 125.62, 127.03, 127.71, 130.72, 133.80, 137.63; 148.88; LC-MS, MS m/z 213 (M++H). |
| 81% | Stage #1: 4-bromo-1,7-dichloroisoquinoline With n-butyllithium In tetrahydrofuran; hexanes at -78 - -65℃; for 0.75h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexanes at -65℃; for 0.666667h; | 2.7 Step 7: To a slurry of the product of Step 6, Example 2 (22.16 g, 80 mmol) in THF (500 ml) at -78° C. was added 100 ml of 1.6 M n-BuLi (in hexanes, 160 mmol) dropwise via cannula over 15 min (maintaining the internal temperature <-65° C.). The resulting solution was stirred for 0.5 h, after such time, (i-PrO)3B (37 ml, 160 mmol) was added dropwise via syringe over 10 min (maintaining the internal temperature <-65° C.). The resulting reaction mixture was stirred for 0.5 h. After checking the reaction by LC/MS for completion, 80 ml of 30% H2O2 (776 mmol) was added dropwise via addition funnel over 10 min (the internal temperature rose to -60° C. during addition), followed by addition of 80 ml of 1 N NaOH (80 mmol). The cooling bath was removed, and the reaction mixture was allowed to warm to room temperature and stirred at room temperature for additional 1 h. After conforming the completion of the reaction by LC/MS, the reaction mixture was then cooled to -40° C., and a solution of 100 g of Na2SO3 (0.793 moles) in 400 ml of water was added dropwise via addition funnel as a means to quench excess H2O2 over 30 min (maintaining the internal temperature 5-10° C.). The resulting slurry was then neutralized with 6 N HCl (approximately 50 ml) at 0° C. till pH 6, then diluted with 500 ml of EtOAc and decanted to a 2 L separatory funnel. To the remaining solid in the reaction vessel was added 500 mL of water and 300 ml of EtOAc, then neutralized with 6 N HCl (approximately 20 ml). The combined organic layers were washed with brine (300 ml×3), then water (200 ml×3), dried over MgSO4 and concentrated to give a crude product which was triturated with 50 ml of EtOAc. The solid was collected by filtration, rinsed with EtOAc (3×25 ml) and dried to give desired product (2 runs: 12.0 g, 70% and 13.8 g, 81%). The filtrates were combined, concentrated and purified by Biotage eluted with 35% EtOAc in hexanes to give 2.1 g of product. Overall, 44.4 g of bromide gave 27.9 g (81%) of 4-OH product. 1H NMR (400 MHz, CD3OD) δ ppm 4.05 (s, 3H), 7.4 (s, 1H), 7.76 (dd, J=8.8, 2, Hz, 1H), 8.16 (d, J=2 Hz, 1H), 8.23 (d, J=8.8 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ ppm 123.78, 124.66, 125.62, 127.03, 127.71, 130.72, 133.80, 137.63; 148.88; LC-MS, MS m/z 213. |
| 70% | Stage #1: 4-bromo-1,7-dichloroisoquinoline With n-butyllithium In tetrahydrofuran; hexanes at -78 - -65℃; for 0.75h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexanes at -78 - -65℃; for 0.666667h; Stage #3: With hydrogenchloride; sodium hydroxide; dihydrogen peroxide; sodium sulfite more than 3 stages; | 22.7 Step 7:; To a slurry of the product of Step 6 (22.16 g, 80 mmol) in THF (500 ml) at -78° C. was added 100 ml of 1.6 M n-BuLi (in hexanes, 160 mmol) dropwise via cannula over 15 min (maintaining the internal temperature <-65° C.). The resulting solution was stirred for 0.5 h, after such time, (i-PrO)3B (37 ml, 160 mmol) was added dropwise via syringe over 10 min (maintaining the internal temperature <-65° C.). The resulting reaction mixture was stirred for 0.5 h. After checking the reaction by LC/MS for completion, 80 ml of 30% H2O2 (776 mmol) was added dropwise via addition funnel over 10 min (the internal temperature rose to -60° C. during addition), followed by addition of 80 ml of 1 N NaOH (80 mmol). The cooling bath was removed, and the reaction mixture was allowed to warm to room temperature and stirred at room temperature for additional 1 h. After conforming the completion of the reaction by LC/MS, the reaction mixture was then cooled to -40° C., and a solution of 100 g of Na2SO3 (0.793 moles) in 400 ml of water was added dropwise via addition funnel as a means to quench excess H2O2 over 30 min (maintaining the internal temperature 5-10° C.). The resulting slurry was then neutralized with 6 N HCl (approximately 50 ml) at 0C till pH 6, then diluted with 500 ml of EtOAc and decanted to a 2 L separatory funnel. To the remaining solid in the reaction vessel was added 500 mL of water and 300 ml of EtOAc, then neutralized with 6 N HCl (approximately 20 ml). The combined organic layers were washed with brine (300 ml×3), then water (200 ml×3), dried over MgSO4 and concentrated to give a crude product which was triturated with 50 ml of EtOAc. The solid was collected by filtration, rinsed with EtOAc (3×25 ml) and dried to give desired product (2 runs: 12.0 g, 70% and 13.8 g, 81%). The filtrates were combined, concentrated and purified by Biotage eluted with 35% EtOAc in hexanes to give 2.1 g of product. Overall, 44.4 g of bromide gave 27.9 g (81%) of 4-OH product.1H NMR (400 MHz, CD3OD) δ ppm 4.05 (s, 3H), 7.4 (s, 1H), 7.76 (dd, J=8.8, 2, Hz, 1H), 8.16 (d, J=2 Hz, 1H), 8.23 (d, J=8.8 Hz, 1H); 13C NMR (100 MHz, DMSO-D6) δ ppm 123.78, 124.66, 125.62, 127.03, 127.71, 130.72, 133.80, 137.63; 148.88; LC-MS, MS m/z 213. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 73% | With trichlorophosphate for 5h; Reflux; Inert atmosphere; | |
| Stage #1: 4-bromo-7-chloroisoquinolin-1-ol With trichlorophosphate for 5h; Reflux; Stage #2: With sodium hydroxide In dichloromethane; water at -35℃; | 6.1.6 A heterogeneous solution of the product of Step 5 (47 g, 182 mmol) in POCl3 (200 mL, 2.15 mol) was slowly heated to reflux over a period of 1 h. The reaction mixture was maintained at reflux for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo to remove excess POCl3. The resulting residue was then taken up into 600 mL of CH2Cl2, cooled to at -35° C., then slowly treated with 1 N NaOH (400 mL) until the mixture was slightly basic (pH=8). The resulting organic layer was separated, washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The resulting residue was crystallized from EtOAc (approximately 50 mL) to give 32 g of desired product. The collected solid was washed with 10% EtOAc/Hexanes (3×50 mL).The mother liquors were concentrated and purified by flash column chromatography (SiO2, eluted with 16% EtOAc in hexanes) to give 4 g of the desired product as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.80 (dd, J=8.81, 2.01 Hz, 1H), 8.14 (d, J=9.06 Hz, 1H), 8.34 (d, J=1.76 Hz, 1H), 8.48 (s, 1H); 13C NMR (100 MHz, DMSO-D6) δ ppm 118.39, 125.06, 127.59, 128.71, 133.89, 134.14, 134.93, 143.18, 148.98; LC-MS, MS m/z 275 (M++H). | |
| Stage #1: 4-bromo-7-chloroisoquinolin-1-ol With trichlorophosphate for 5h; Reflux; Stage #2: With sodium hydroxide In dichloromethane; water | 2.6 Step 6:A heterogeneous solution of the product of Step 5, Example 2 (47 g, 182 mmol) in POCl3 (200 mL, 2.15 mol) slowly heated to reflux over a period of 1 h. The reaction mixture was maintained at reflux for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo to remove excess POCl3. The resulting residue was then taken-up into 600 mL of CH2Cl2, cooled to at -35° C., then neutralized carefully with 1 N NaOH (400 mL) until the mixture was slightly basic (pH=8). The resulting organic layer was separated, washed with water, dried over MgSO4 and concentrated in vacuo. The resulting residue was crystallized from EtOAc (approximately 50 mL) to give 32 g of desired product. The collected solid was washed with 10% EtOAc/Hexanes (3×50 ml). The mother liquid was concentrated and purified by Biotage (elution with 16% EtOAc in hexanes) to give 4 g of the desired product as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.80 (dd, J=8.81, 2.01 Hz, 1H), 8.14 (d, J=9.06 Hz, 1H), 8.34 (d, J=1.76 Hz, 1H), 8.48 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ ppm 118.39, 125.06, 127.59, 128.71, 133.89, 134.14, 134.93, 143.18, 148.98; LC-MS, MS m/z 275. |
| Stage #1: 4-bromo-7-chloroisoquinolin-1-ol With trichlorophosphate for 5h; Heating / reflux; Stage #2: With sodium hydroxide In dichloromethane; water at -35℃; | 22.6 Step 6:; A heterogeneous solution of the product of Step 5 (47 g, 182 mmol) in POCl3 (200 mL, 2.15 mol) slowly heated to reflux over a period of 1 h. The reaction mixture was maintained at reflux for 4 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo to remove excess POCl3. The resulting residue was then taken-up into 600 mL of CH2Cl2, cooled to at -35° C., then neutralized carefully with 1 N NaOH (400 mL) until the mixture was slightly basic (pH=8). The resulting organic layer was separated, washed with water, dried over MgSO4 and concentrated in vacuo. The resulting residue was crystallized from EtOAc (approximately 50 mL) to give 32 g of desired product. The collected solid was washed with 10% EtOAc/Hexanes (3×50 ml).The mother liquid was concentrated and purified by Biotage (elution with 16% EtOAc in hexanes) to give 4 g of the desired product as a solid.1H NMR (400 MHz, CDCl3) δ ppm 7.80 (dd, J=8.81, 2.01 Hz, 1H), 8.14 (d, J=9.06 Hz, 1H), 8.34 (d, J=1.76 Hz, 1H), 8.48 (s, 1H); 13C NMR (100 MHz, DMSO-D6) δ ppm 118.39, 125.06, 127.59, 128.71, 133.89, 134.14, 134.93, 143.18, 148.98; LC-MS, MS m/z 275. |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1.1: triethylamine / benzene / 2 h 1.2: 3.5 h / 90 °C / Reflux 2.1: N-Bromosuccinimide / acetonitrile / Reflux 3.1: trichlorophosphate / 5 h / Reflux 3.2: -35 °C / pH 8 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / Reflux 2.1: trichlorophosphate / 5 h / Reflux 2.2: -35 °C / pH 8 |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1.1: n-butyllithium; Triisopropyl borate / hexane; tetrahydrofuran / 0.75 h / -78 - -65 °C 1.2: 1.17 h / -60 - 20 °C 1.3: 0 °C / pH 6 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C | ||
| Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C / Inert atmosphere | ||
| Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 4 °C / Inert atmosphere |
| Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.75 h / -78 - -65 °C 1.2: 0.67 h / -78 - -65 °C 2.1: methanol; hexanes; acetonitrile / 14 h / 0 - 20 °C |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 6 steps 1.1: n-butyllithium; Triisopropyl borate / hexane; tetrahydrofuran / 0.75 h / -78 - -65 °C 1.2: 1.17 h / -60 - 20 °C 1.3: 0 °C / pH 6 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 10 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / 16 h 5.1: hydrogenchloride / water; methanol / 2 h / Reflux 6.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 0 - 20 °C | ||
| Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / Sonication; Inert atmosphere 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / Inert atmosphere 5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere | ||
| Multi-step reaction with 5 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 4 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / Sonication; Inert atmosphere 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / Inert atmosphere 5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 4 steps 1.1: n-butyllithium; Triisopropyl borate / hexane; tetrahydrofuran / 0.75 h / -78 - -65 °C 1.2: 1.17 h / -60 - 20 °C 1.3: 0 °C / pH 6 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 10 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / 16 h | ||
| Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / Sonication; Inert atmosphere 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / Inert atmosphere | ||
| Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 4 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / Sonication; Inert atmosphere 4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1.1: n-butyllithium; Triisopropyl borate / hexane; tetrahydrofuran / 0.75 h / -78 - -65 °C 1.2: 1.17 h / -60 - 20 °C 1.3: 0 °C / pH 6 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 10 - 20 °C | ||
| Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / Sonication; Inert atmosphere | ||
| Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / 65 °C / Inert atmosphere 1.2: 0.75 h / 65 °C / Inert atmosphere 1.3: 0.5 h / -60 - -40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 4 °C / Inert atmosphere 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 3.5 h / 10 - 20 °C / Sonication; Inert atmosphere |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 7 steps 1.1: n-butyllithium; Triisopropyl borate / hexane; tetrahydrofuran / 0.75 h / -78 - -65 °C 1.2: 1.17 h / -60 - 20 °C 1.3: 0 °C / pH 6 2.1: diazomethyl-trimethyl-silane / hexane; acetonitrile / 14 h / 0 - 20 °C 3.1: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 10 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; HATU / 16 h 5.1: hydrogenchloride / water; methanol / 2 h / Reflux 6.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 16 h / 0 - 20 °C 7.1: hydrogenchloride / 1,4-dioxane; water / 3 h / 25 °C |