Structure of 1376676-65-1
*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 !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
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) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
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) ]}
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
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
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. : | 1376676-65-1 |
Formula : | C10H13N3 |
M.W : | 175.23 |
SMILES Code : | CC1=C2C=CC(NC)=CC2=NN1C |
MDL No. : | MFCD24567305 |
InChI Key : | JTKWSKSSIYFOAA-UHFFFAOYSA-N |
Pubchem ID : | 67813064 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* 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 |
---|---|---|
37.1% | Sodium methoxide (1.8g, 33.3mmol) in anhydrous methanol (60mL) solution,obtained in Example 1 was added at once 2,3-dimethyl--2H- indazol-6-amine(1.6g, 10mmol), stirring at room temperature was added paraformaldehyde (0.6g,20mmol), the reaction was refluxed for 2h, stirring continued at roomtemperature 2h, temperature was lowered to 0 C, 10 C or less, in themixture was added portionwise NaBH 4 (0.76g, 20mmol) , 40 C reaction 3h, thecrude oil was cooled to room temperature and stirring was continued overnight,concentrated to remove methanol, aqueous layer was extracted with ethylacetate, the organic layer was washed with water, dried over anhydrous sodiumsulfate, filtered, and concentrated to yield. A silica gel column (methylenechloride: methanol = 20: 1) to give a white solid 0.65g, yield 37.1%. | |
Sodium methoxide (19 gm) was dissolved in methanol (610 ml) and then added 2,3-dimethyl-2H-indazol-6-amine (13 gm). The reaction mixture was stirred for 15 minutes and then added paraformaldehyde (3.9 gm). The contents were heated to 60C and stirred for 10 hours. The reaction mass was then cooled to room temperature and maintained for 4 hours 30 minutes. Sodium borohydride (2.8 gm) was added to the reaction mass slowly at room temperature and then heated to reflux. The reaction mass was maintained for 2 hours at reflux and then cooled to room temperature. The reaction mass was stirred for 14 hours at room temperature and then added sodium hydroxide solution (1M, 100 ml). The pH of the reaction mass was adjusted to 8.0 to 8.5 with hydrochloric acid solution (40 ml) and then added ethyl acetate (400 ml). Then the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate and treated with carbon. The combined organic layers were washed with sodium chloride solution and dried with sodium sulfate. The organic layer was treated with carbon and filtered through hi-flow bed. The solvent was distilled off under vacuum at below 50C to obtain a residual mass. To the residual mass was added diisopropyl ether (75 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 10 gm of N,2,3-trimethyl-2H-indazol-6-amine. | ||
10 g | Sodium methoxide (19 gm) was dissolved in methanol (610 ml) and then added 2,3-dimethyl-2H-indazol-6-amine (13 gm). The reaction mixture was stirred for 15 minutes and then added paraformaldehyde (3.9 gm). The contents were heated to 60 C. and stirred for 10 hours. The reaction mass was then cooled to room temperature and maintained for 4 hours 30 minutes. Sodium borohydride (2.8 gm) was added to the reaction mass slowly at room temperature and then heated to reflux. The reaction mass was maintained for 2 hours at reflux and then cooled to room temperature. The reaction mass was stirred for 14 hours at room temperature and then added sodium hydroxide solution (1M, 100 ml). The pH of the reaction mass was adjusted to 8.0 to 8.5 with hydrochloric acid solution (40 ml) and then added ethyl acetate (400 ml). Then the layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried with sodium sulfate and treated with carbon. The combined organic layers were washed with sodium chloride solution and dried with sodium sulfate. The organic layer was treated with carbon and filtered through hi-flow bed. The solvent was distilled off under vacuum at below 50 C. to obtain a residual mass. To the residual mass was added diisopropyl ether (75 ml) and stirred for 1 hour, filtered. The solid obtained was dried to give 10 gm of N,2,3-trimethyl-2H-indazol-6-amine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5-(4-Chloropyrimidin-2ylamino)-2-methylbenzenesulfonamide (17 gm) as obtained in example 1, <strong>[1376676-65-1]N,2,3-trimethyl-2H-indazol-6-amine</strong> (10 gm) as obtained in example 2 and ethanol (166 ml) were added at room temperature and then heated to reflux. The reaction mass was maintained for 3 hours at reflux and then added concentrated hydrochloric acid (1 ml). The reaction mass was maintained for 10 hours at reflux and then cooled to room temperature. The separated solid was filtered and dried to obtain 17 gm of pazopanib hydrochloride (HPLC Purity: 97.5%). | ||
17 g | 5-(4-Chloropyrimidin-2ylamino)-2-methylbenzenesulfonamide (17 gm) as obtained in example 1, <strong>[1376676-65-1]N,2,3-trimethyl-2H-indazol-6-amine</strong> (10 gm) as obtained in example 2 and ethanol (166 ml) were added at room temperature and then heated to reflux. The reaction mass was maintained for 3 hours at reflux and then added concentrated hydrochloric acid (1 ml). The reaction mass was maintained for 10 hours at reflux and then cooled to room temperature. The separated solid was filtered and dried to obtain 17 gm of pazopanib hydrochloride (HPLC Purity: 97.5%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.6% | With sodium hydrogencarbonate; In tetrahydrofuran; ethanol; for 20h;Reflux; | Formula III (5 g, 0.029 mol)And sodium bicarbonate (7.2 g, 0.086 mol)Was added to THF (20 ml)And absolute ethanol (80 ml).2,4-dichloropyrimidine (12.8 g, 0.086 mol) was added at room temperature,Heated to reflux for 20 h.The reaction was cooled to room temperature,filter,The filter cake was washed with absolute ethanol (20 ml x 2).The filtrates were combined,After concentration under reduced pressure to dryness, isopropyl ether (60 ml)And toluene (30 ml) were mixed,Stirred at room temperature for 1 h,filter,The filter cake was dried to give pale yellow solid 7 (6.7 g, 81.6%), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.6 g | With sodium tetrahydroborate; In methanol; for 3h;Reflux; | Sodium borohydride (3.68, 0.093 11 01) was added in portions,The mixture was heated to reflux for 3 hours.The reaction was cooled to room temperature,The reaction was concentrated to dryness,Ethyl acetate (50 ml) and water (30 ml) were added,After separation of the organic layer,The aqueous layer was extracted with ethyl acetate (20 ml of X2)The organic layers were combined,The solvent was distilled off under reduced pressure, followed by recrystallization from ethyl acetate (35 ml)To give an off-white solid (4.6g, 84.6%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; | The compound of formula 7,Triphenylphosphine, methylene chloride and dichlorodicyanobenzoquinone were added to the reaction flask.Methanol was added dropwise to the reaction solution. After the reaction was completed, an aqueous sodium thiosulfate solution was added and the layers were separated. The organic phase was washed with saturated brine.Then, methanol was added and it was reduced to 0 degree. After stirring for 1-2 hours, the solid was precipitated as a compound of Formula 2, with a yield of 94% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N-ethyl-N,N-diisopropylamine; In toluene; at 40℃; | 2,4-Dichloro-5-nitropyrimidine 5.0 g, compound of formula 2 (0.95 eq), diisopropylethylamine and 100 mL at room temperature toluene was added to the reaction flask, heated, and reacted at 40C for 4-6 hours. TLC was controlled and the reaction was completed.Wash with saturated saline,Dry with anhydrous sodium sulfate, concentrate under reduced pressure, cool to 0-5 C, add methyl tert-butyl ether under stirring, precipitate solid, continue stirring at this temperature for 30 minutes, filter and drain to obtain The compound of formula 3 has a yield of 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In particular, the TKI may be Pazopanib. While any pharmaceutically acceptable salt is contemplated herein, particular examples of salt forms of TKIs, which are contemplated in accordance with the present invention, include: Pazopanib 5-(4-chloropyrimidin-2ylamino)-2-methylbenzenesulfonamideN,2,3-trimethyl-2H-indazol-6-amine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydrogencarbonate; In ethanol; at 75 - 78℃; for 4h; | Add 22.5g (0.1mol) 6-bromo-2,3-dimethyl-2H-indazole and 400ml ethanol to a 1L reaction flask, stir add 10.1g (0.15mol) monomethylamine hydrochloride, add 25.2g ( 0.3 mol) sodium bicarbonate, the temperature is raised to 75-78C, and the reaction is carried out for 4 hours. Cool to room temperature, filter the resulting reaction solution, concentrate the mother liquor, add 200 mL ethyl acetate and 200 mL water, stir and separate the layers, and then extract the aqueous layer twice with 200 mL ethyl acetate, each with 100 mL, combine the ethyl acetate layers, reduce press and concentrate to dryness. The obtained residue was recrystallized by adding 120 mL of ethyl acetate to obtain 15.8 g of off-white solid with a molar yield of 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With copper(I) oxide; In N,N-dimethyl-formamide; at 100℃; | A flask was charged with 6-bromo-2,3-dimethyl-2H-indazole (1 eq.), methylamine (2 eq.), CU2O (5 mol%) and Ν,Ν-dimethylformamide. The reaction mixture was stirred at 100 C until completion of the reaction. Then, the reaction mixture was cooled to room temperature and water was added. The mixture was extracted with dichloromethane. Organic layer was separated and dried with anhydrous sodium sulfate. The solvent was removed in vacuo to obtain oily residue. Diethyl ether was added onto the oily residue and stirred for 2 h for crystallization. Product crystals were collected by filtration, washed with diethyl ether and dried to afford a brownish powder (Yield: 97%; LC-purity: 99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.94% | step 1: Add 19.76g of 2,3-dimethyl-6-aminoindazole hydrochloride to a 500ml reaction flask,10.08g sodium methoxide and 200ml methanol,The reaction was heated to reflux for 0.5h,Add 6.01g of paraformaldehyde while it is still hot,React at room temperature for 3 to 4 hours,TLC monitored the reaction.After 2,3-dimethyl-6-aminoindazole has been converted,Slowly add 7.58g of sodium borohydride in portions,The reflux reaction is completed for 3 to 4 hours.After the reaction is over,Spin dry solvent,Add 100ml of water and 100ml of dichloromethane to the residue of the kettle for liquid separation,The aqueous phase was extracted once with dichloromethane,The organic phases were combined and washed with purified water until neutral.dried over anhydrous sodium sulfate,filter desiccant,After the filtrate was spin-dried, 100 ml of isopropyl ether was added to make a slurry at room temperature for 1 h.After filtering, the filter cake was dried to constant weight to obtain 16.46g of pale yellow solid,is N,2,3-trimethyl-2H-indazol-6-amine,Yield 93.94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | With hydrogenchloride; In isopropanol;Reflux; | Step 3: Add 20.40g of N-(2-chloropyrimidin-4-yl)-<strong>[1376676-65-1]N,2,3-trimethyl-2H-indazol-6-amine</strong> into a 500ml reaction flask,9.95g <strong>[1376676-65-1]N,2,3-trimethyl-2H-indazol-6-amine</strong>;200ml isopropanol and 10.50ml concentrated hydrochloric acid,The reaction was heated to reflux for 3 to 4 hours, and the progress of the reaction was monitored by TLC.After the reaction was completed, it was cooled to room temperature,suction filtration,The filter cake is rinsed with a small amount of frozen isopropanol,The solvent was sucked dry, and the filter cake was dried to constant weight to obtain 23.7 g of a pale yellow solid.The dried solid was added to 360ml of ethylene glycol dimethyl ether,Heated to 85C to dissolve,Stir for 15min,Then cooled to room temperature to precipitate crystals,filter,The filter cake was dried to constant weight at 60C to obtain an off-white solid, namely N2,N4bis(2,3-dimethyl-2H-indazol-6-yl)-N2,N4-dimethylpyrimidine-2,4-diamine hydrochloride 20.15g, Yield 76.50%. |