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[ CAS No. 1693758-51-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1693758-51-8
Chemical Structure| 1693758-51-8
Structure of 1693758-51-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1693758-51-8 ]

CAS No. :1693758-51-8 MDL No. :MFCD30533720
Formula : C30H24N8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XUMALORDVCFWKV-IBGZPJMESA-N
M.W : 528.56 Pubchem ID :91933883
Synonyms :
IPI-549

Calculated chemistry of [ 1693758-51-8 ]

Physicochemical Properties

Num. heavy atoms : 40
Num. arom. heavy atoms : 30
Fraction Csp3 : 0.1
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 152.25
TPSA : 125.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.56
Log Po/w (XLOGP3) : 3.2
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 3.05

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.36
Solubility : 0.00232 mg/ml ; 0.00000438 mol/l
Class : Moderately soluble
Log S (Ali) : -5.5
Solubility : 0.00167 mg/ml ; 0.00000317 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.0
Solubility : 0.00000531 mg/ml ; 0.00000001 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.42

Safety of [ 1693758-51-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1693758-51-8 ]

* 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 [ 1693758-51-8 ]

[ 1693758-51-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1466563-97-2 ]
  • [ 39806-89-8 ]
  • 2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With trans-bis(acetonitrile)palladium(II) chloride; caesium carbonate; XPhos at 85℃; for 1.5h; Inert atmosphere; Sealed tube;
With dichloro bis(acetonitrile) palladium(II); caesium carbonate; XPhos at 85℃; for 1.5h; Inert atmosphere; Sealed tube; 1 Example 1 [00658] Amide B was placed in a sealed tube (0.67 mmol, 1.0 equiv) followed by dichlorobis(acetonitrile)palladium (15 mol%), X-Phos (45 mol%), and cesium carbonate (3.0 equiv) Propionitrile (5 mL) was added and the mixture was bubbled with Ar for 1 mi 4-Ethynyl- 1-methyl-i H-pyrazole (1.24 equiv) was added and the resulting orange mixture was sealed and stirred in an oil bath at 85 oC for 1 .5h. The resulting brownish-black mixture was allowed to cool at which point there was no more SM by LC/MS analysis. The mixture was then filtered through a short plug of cotton using acetonitrile and methylene chloride. The combined filtrates were concentrated onto silica gel and purified using flash silica gel chromatography (Combiflash, 4g column, gradient of 0-5% methylene chloride/methanol). The resulting material was further purified by reverse phase HPLC (15-90% acetonitrile with 0.1% formic acid/water with 0.1% formic water) to provide desired compound 4. ESI-MS mlz: 529.5 [M+H]+.
With dichloro bis(acetonitrile) palladium(II); caesium carbonate; XPhos at 85℃; for 1.5h; Sealed tube; Inert atmosphere; 1 [001314] Amide B was placed in a sealed tube (0.67 mmol, 1.0 equiv) followed by dichlorobis(acetonitrile)palladium (15 mol%), X-Phos (45 mol%), and cesium carbonate (3.0 equiv) Propionitrile (5 mL) was added and the mixture was bubbled with Ar for 1 min. 4-Ethynyl-l -methyl- 1H- pyrazole (1.24 equiv) was added and the resulting orange mixture was sealed and stirred in an oil bath at 85 oC for 1.5h. The resulting brownish-black mixture was allowed to cool at which point there was no more SM by LC/MS analysis. The mixture was then filtered through a short plug of cotton using acetonitrile and methylene chloride. The combined filtrates were concentrated onto silica gel and purified using flash silica gel chromatography (Combiflash, 4g column, gradient of 0-5% methylene chloride/methanol). The resulting material was further purified by reverse phase HPLC (15-90% acetonitrile with 0.1% formic acid/water with 0.1% formic water) to provide desired compound 4. ESI- MS m/z: 529.5 [M+H]+.
With dichloro bis(acetonitrile) palladium(II); caesium carbonate; propiononitrile; XPhos at 85℃; for 1.5h; Inert atmosphere; Sealed tube; 1.A Example 1. Preparation of Compound 1 Amide B was placed in a sealed tube (0.67 mmol, 1.0 equiv) followed by dichlorobis(acetonitrile)palladium (15 mol%), X-Phos (45 mol%), and cesium carbonate (3.0 equiv) Propionitrile (5 mL) was added and the mixture was bubbled with Ar for 1 mi 4-Ethynyl- 1-methyl- 1H-pyrazole (1.24 equiv) was added and the resulting orange mixture was sealed and stirred in an oil bath at 85 °C for 1 .5h. The resulting brownish-black mixture was allowed to cool at which point there was no more SM by LC/MS analysis. The mixture was then filtered through a short plug of cotton using acetonitrile and methylene chloride. The combined filtrates were concentrated onto silica gel and purified using flash silica gel chromatography (Combiflash, 4g column, gradient of 0-5% methylene chloride/methanol). The resulting material was fUrther purified by reverse phase HPLC (15-90% acetonitrile with 0.1% formic acid/water with 0.1% formic water) to provide desired Compound 1. The solution containing Compound 1 was lyophilized to give amorphous Compound 1. ESI-MS m/z: 529.5 [M+Hj+.

  • 2
  • [ 1693758-51-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; for 41h; 28 Example 28 Example 28 [00703] Compound 4 (0.12 mmol, 1.0 equiv) was dissolved in a mixture of ethanol and ethyl acetate (20mL, 3:1 v/v). Palladium on carbon (19 mg, 10% Pd) was added and the reaction was placed under an atmosphere of H2. The mixture was stirred at RT for 4 lh after which it was filtered through a filter disk, concentrated and purified by flash silica gel chromatography (Combiflash, 4g Si column, gradient of 0-5% methanol/methylene chloride) toprovide alkene 53. ESI-MS m/z: 531.6 [M+H]t
With palladium 10% on activated carbon; hydrogen In ethanol; ethyl acetate at 20℃; for 41h; 28 Example 28 [001359] Compound 4 (0.12 mmol, 1.0 equiv) was dissolved in a mixture of ethanol and ethyl acetate (20 mL, 3 : 1 v/v). Palladium on carbon (19 mg, 10% Pd) was added and the reaction was placed under an atmosphere of H2. The mixture was stirred at RT for 41h after which it was filtered through a filter disk, concentrated and purified by flash silica gel chromatography (Combiflash, 4g Si column, gradient of 0-5% methanol/methylene chloride) to provide alkene 53. ESI-MS m/z: 531.6 [M+H]+.
  • 3
  • [ 1350643-72-9 ]
  • 2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 4
  • [ 1383056-73-2 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.03 h / 20 °C 1.2: 22 h 1.3: 0.5 h / 20 °C 2.1: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 3 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 22 h / 20 °C 2: trifluoroacetic acid / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 0.5 h / 20 °C 3: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Sealed tube; Inert atmosphere
Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.03 h / 23 °C 1.2: 22 h / 23 °C 2.1: trifluoroacetic acid / dichloromethane / 0.5 h / 23 °C 3.1: trans-bis(acetonitrile)palladium(II) chloride; XPhos; caesium carbonate / 1.5 h / 85 °C / Inert atmosphere; Sealed tube
  • 5
  • [ 21327-86-6 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C 1.2: 2 h / 20 - 40 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - -10 °C / Inert atmosphere 2.2: 2 h / -30 - -10 °C / Inert atmosphere 2.3: 1 h / Reflux 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.03 h / 20 °C 3.2: 22 h 3.3: 0.5 h / 20 °C 4.1: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 1.2: 2 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -30 - -10 °C / Inert atmosphere 2.2: 1 h / -15 °C / Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 22 h / 20 °C 4.1: trifluoroacetic acid / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 0.5 h / 20 °C 5.1: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Sealed tube; Inert atmosphere
  • 6
  • [ 62-53-3 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C 1.2: 2 h / 20 - 40 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - -10 °C / Inert atmosphere 2.2: 2 h / -30 - -10 °C / Inert atmosphere 2.3: 1 h / Reflux 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.03 h / 20 °C 3.2: 22 h 3.3: 0.5 h / 20 °C 4.1: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 5 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 1.2: 2 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -30 - -10 °C / Inert atmosphere 2.2: 1 h / -15 °C / Inert atmosphere 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 22 h / 20 °C 4.1: trifluoroacetic acid / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 0.5 h / 20 °C 5.1: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Sealed tube; Inert atmosphere
  • 7
  • [ 1386861-46-6 ]
  • 2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 8
  • [ 1466563-96-1 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trifluoroacetic acid / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 0.5 h / 20 °C 2: dichloro bis(acetonitrile) palladium(II); XPhos; caesium carbonate / 1.5 h / 85 °C / Sealed tube; Inert atmosphere
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 0.5 h / 23 °C 2: trans-bis(acetonitrile)palladium(II) chloride; XPhos; caesium carbonate / 1.5 h / 85 °C / Inert atmosphere; Sealed tube
  • 9
  • [ 39806-89-8 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: XPhos; caesium carbonate; dichloro bis(acetonitrile) palladium(II) / acetonitrile / 3 h / 70 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: XPhos; caesium carbonate; dichloro bis(acetonitrile) palladium(II) / acetonitrile / 3 h / 70 °C / Inert atmosphere 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 30 °C / Inert atmosphere
  • 10
  • [ 1394003-86-1 ]
  • [ 2089424-04-2 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
70% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 30℃; for 16h; Inert atmosphere; 1.B Example 1. Preparation of Compound 1 The second step is an amide coupling reaction between Compound C and the carboxylic acid employing EDCI and HOBt at 30°C. Compound C was treated with the carboxylic acid, HOBt, EDCI and DIPEA ill DMF and stirred at 30CC under nitrogen until judged complete by HPLC. The reaction mixture was polish filtered and pumped slowly mto a 0. 1M potassium carbonate aq. solutioll. After ageing, the resulting suspension was filtered. The crude Compound 1 was subsequently purified by recrystallization. The solid was dissolved in a mixture of hot IPA/water (1:1) and treated with water. On cooling Compound 1 precipitated from solution. The crystals were isolated by filtration, washed with water and dried. Typical chemical purity is > 98 % area. Typical yields are 60 - 70%. Specifically, the reaction vessel was charged with Compound C (1 wt, 1 equ.), 2- aminopyrazolo[1,5-ajpynmidinecarboxylic acid (1.05 equ), 1-hydroxybenzotriazole hydrate (0.1 equ.), 1-ethyl-(3- dimethylaminopropyl)carbodiimide hydrochloride, anhydrous (1.2 equ.), N,N-dimethylformamide, ACS grade (10 volumes), and N,N-diisopropylethylamine, ReagentPlus (3 equ.) at r.t. (22 + 3 °C) with under nitrogen at r.t.. The reaction mixture was heated at 30 + 5°C under nitrogen. The reaction was stirred at 30 ± 5°C (Target 30 °C). The reaction was monitored by HPLC after 16 hours. This reaction could also be conducted without the base ,Ndiisopropylethylamine. The reaction mixture was quenched as follows. A 0. 1M solution of potassium carbonate in water was prepared. The quench vessel was charged with potassium carbonate (3.2 equ) followed by water (80 volumes). The mixture was stirred at r.t. until fully dissolved. The DMF reaction solution (product layer) was polish filtered. The reaction vessel was rinsed with a small amount of DMF (0.5 volumes). The DMF rinse was passed through the polish filter. The DMF solution (product layer) was slowly transferred into the potassium carbonate solution over 2 hours at r.t (22 ± 3 °C). The suspension was aged for 1 hour at r.t. (22 ± 3 °C). The solid was filtered off under house vacuum (table top filter), de-liquored and washed with water (2 x 10 volumes). It was deliquored under vacuum at r.t. until constant weight was achieved. A vessel was charged with crude Compound 1, isopropyl alcohol (10 volumes) followed by water (10 volumes). The mixture was agitated. The suspension was heated to 80 + 3 °C (Target 80 °C). The mixture was aged for 15 minutes. Water (10 volumes) was charged to the vessel at such a rate to maintain the internal temperature between 80 ± 5 °C (Target 80 °C).The internal temperature was adjusted to 80 °C and held for 20 minutes before proceeding to the next step. The suspension was cooled to r.t. (22 ± 3 °C) over 4 hours. The suspension was aged at r.t. for 4 hours. The solid was filtered under vacuum. The solid was washed with 20% isopropyl alcohol in water (2 x 5 volumes). The solid was deliquored under vacuum for 1 hour. The solid was transferred to diying trays and placed in a vacuum oven and dry at 40 °C under vacuum, with a nitrogen bleed, until constant weight was achieved. Characterization of the solid showed it was Form 1.
  • 11
  • [ 2089424-04-2 ]
  • [ 2089424-02-0 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
85% With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; Inert atmosphere; 1.C Example 1. Preparation of Compound 1 The coupling of compound C with compound D was carried out as follows. The reaction vessel was evacuated and purged with nitrogen for? 15 minutes. Compound C (1 wt, 1 equ.), Compound D (1.05 equ.) and acetonitrile (15 volumes), were charged to the reaction vessel at 22 + 3°C, under nitrogen. The reaction vessel was evacuated and back filled with nitrogen. The mixture was agitated. N,N-Diisopropylethylamine (DIPEA) (1.1 equ.) at 22 + 3°C was charged to the reaction vessel under nitrogen. The reaction mixture was heated to 60 + 2°C and stirred under nitrogen. The reaction was monitored by HPLC. once the reaction was judged complete by HPLC a 1M solution of potassium hydroxide (0.5 equ., 1.21 volumes) was charged to the reaction vessel at such a rate to maintain an internal temperature between 52 - 60°C. The suspension was aged at 60 + 2°C for 2 hours, then cooled to 22 + 3°C over 1 hour. The solid was filtered off under vacuum then washed with acetonitrile (2 x 2.5 volumes) followed by 4:1/water: acetonitrile (2 x 2.5 volumes). It was deliquored under vacuum at r.t. for ? 12 hours. Water (8 volumes), crnde compound 1 (1 xvi) from and acetone (32 volumes) were charged to the recrystallization vessel. The mixture was agitated and heated to 55 + 5°C. The solution was aged at 55 + 5°C (Target 50°C) for 10 minutes and then cooled the solution to 23 + 3°C. The reaction solution was transferred into a holding drnm. The recrystallization vessel was rinsed with acetone (twice). The reflux condenser was exchanged for a short path distillation setup on the recrystallization vessel and flushed with nitrogen for a minimum of 15 minutes. The reaction solution was transferred through an inline polish filter (media PTFE, pore size 1 .tm) back into the recrystallization vessel. Acetone (2 volumes) was charged into the holding drum and the rinses were transferred into the recrystallization vessel through the inline filter. The mixture was agitated and the jacket temperature was set to 45°C. The solvent volume was reduced to 20 volumes under reduced pressure maintaining an internal temperature at? 30°C (Target 35°C). The vacuum was released and a mixture of 3 : 2 / isopropyl alcohol : water (20 volumes) was charged to the recrystallization vessel. The solvent volume was reduced to 20 volumes under reduced pressure maintaining an internal temperature at? 30°C (Target 35°C). The vacuum was released and a mixture of 3 : 2 / isopropyl alcohol : water (20 volumes) was charged to the recrystallization vessel. The solvent volume was reduced to 20 volumes under reduced pressure maintaining an internal temperature at 30°C (Target 35°C). The vacuum was released and a mixture of 3 2 / isopropyl alcohol : water (10 volumes) was charged to the recrystallization vessel. The short path distillation head was replaced with a reflux condenser. The reactor was purged with nitrogen for at least 15 minutes. The stirred suspension was heated to 60 ± 2°C (Target 60°C). The suspension was aged at 60 ± 2°C (Target 60°C) for 14 ± 2 hours and was then cooled to 23 ± 3°C over 1 hour. A small sample was taken to confirm conversion to Form 1 was complete. The suspension was aged for 3 hours. The solid was filtered off under vacuum and washed the solid with 20% isopropyl alcohol in water (2 x 5 volumes). The solid was deliquored under vacuum for 1 hour, transferred to drying trays, placed in a vacuum oven and dried at 40°C under vacuum, with a nitrogen bleed, until constant weight was achieved. Characterization of the solid showed it was Form 1. The typical yield for Method 3 is about 75 - 85%.
  • 12
  • [ 1394003-86-1 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 23 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere
  • 13
  • 2-((tert-butoxycarbonyl)amino)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [ No CAS ]
  • [ 1350643-72-9 ]
  • 2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 14
  • [ 1201657-09-1 ]
  • [ 1693758-51-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / tert-butyl methyl ether; water / 4 h / 15 - 25 °C / Large scale 2: XPhos; caesium carbonate; propiononitrile; dichloro bis(acetonitrile) palladium(II) / 1.5 h / 85 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 3 steps 1: potassium hydroxide / tert-butyl methyl ether; water / 4 h / 15 - 25 °C / Large scale 2: XPhos; caesium carbonate; dichloro bis(acetonitrile) palladium(II) / acetonitrile / 3 h / 70 °C / Inert atmosphere 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 30 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: potassium hydroxide / tert-butyl methyl ether; water / 4 h / 15 - 25 °C / Large scale 2: XPhos; caesium carbonate; dichloro bis(acetonitrile) palladium(II) / acetonitrile / 3 h / 70 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / acetonitrile / 60 °C / Inert atmosphere
  • 15
  • [ 1260169-02-5 ]
  • IPI-549 [ No CAS ]
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