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[ CAS No. 5744-80-9 ] {[proInfo.proName]}

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Chemical Structure| 5744-80-9
Chemical Structure| 5744-80-9
Structure of 5744-80-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5744-80-9 ]

CAS No. :5744-80-9 MDL No. :MFCD09991542
Formula : C5H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NELVNOMSYNLQGQ-UHFFFAOYSA-N
M.W : 175.03 Pubchem ID :21724046
Synonyms :

Calculated chemistry of [ 5744-80-9 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.15
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 1.49
Log Po/w (MLOGP) : 1.17
Log Po/w (SILICOS-IT) : 1.48
Consensus Log Po/w : 1.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.43
Solubility : 0.645 mg/ml ; 0.00369 mol/l
Class : Soluble
Log S (Ali) : -1.65
Solubility : 3.94 mg/ml ; 0.0225 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.03
Solubility : 1.62 mg/ml ; 0.00927 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 5744-80-9 ]

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

Application In Synthesis of [ 5744-80-9 ]

* 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 [ 5744-80-9 ]

[ 5744-80-9 ] Synthesis Path-Downstream   1~20

  • 1
  • ethyl 4-amino-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylate [ No CAS ]
  • [ 5744-80-9 ]
  • sodium 4-((1,5-dimethyl-1H-pyrazol-3-yl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Example 14 In a vessel 36.5 mmol (-42.6 mL) of Compound 29 solution in 2-methyl-2- butanol was combined with 30.7g (65.1 mmol) tetrabutylammonium hydroxide (55 wt% in water), 8.01g (27.0 mmol) Compound 13 , and 10 mL 2-methyl-2-butanol. The mixture was heated at 70 C until hydrolysis of Compound 13 was complete (full dissolution, <15 min). The solution was cooled to 60 C and 1.12g (2.22 mmol) of tBuBippyPhos followed by 384 mg (1.028 mmol) allylpalladium chloride dimer (L:Pd = 1 :1) was added. The mixture was heated to 80 C and was aged at this temperature for 20h before cooling to 22 C. Water was added and the mixture concentrated, a constant volume distillation was then performed to swap to ethanol (40-55 C, 150 mbar). The resulting solution was passed through a 5 micron filter to remove any particulates. The solution was heated to 55 C and 8.10 mL (40.52 mmol, 1.5 equiv) 5N NaOH (aq) was added dropwise over a 3 h period. Crystals of Compound 31 began to form, and after aging for an additional lh, the mixture was cooled to 20 C over 3 h. After an additional 6h of aging, crystals were collected on a frit and the cake was washed with 40 mL of 90: 10 ethanol: water, followed by 48 mL acetone. After drying at 80 C in a vacu-oven for 16 h, Compound 31 was collected as an off-white solid (8.89g, 85%)
  • 2
  • ethyl 4-amino-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]-pyrrolo[2,3-b]pyridine-7-carboxylate acetate [ No CAS ]
  • [ 5744-80-9 ]
  • ethyl 4-((1,5-dimethyl-1H-pyrazol-3-yl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; t-BuBrettPhos; In tert-Amyl alcohol; at 98 - 103℃; for 20h;Inert atmosphere; Example 12 Compound 30 was prepared by the coupling of Compound 22 with Compound 29, 3 -bromo- 1,5 -dimethyl- lH-pyrazole in the presence ofTris(dibenzylideneacetone)dipalladium chloroform adduct, t-Brettphos and potassium phosphate in tert-amyl alcohol at 98-103 C under inert atmosphere. After completion of the reaction (typical level of Int.9 -5% & typical reaction hrs 20 h), the mass was cooled to ambient temperature and t-amyl alcohol (4 Vol) and 20 Vol of water were charged into the reaction mass. The reaction mass was stirred for 15 min. and then phase split. The organic layer was diluted with 10 Vol of MTBE and product was extracted with 20 Vol of 1M methane sulphonic acid. The MSA stream was treated with 15 wt % charcoal to reduce the residual palladium numbers. The filtrate was cooled to below 20 C and the pH was adjusted to 1.7-1.9 using IN NaOH for product crystallization and then iltered. The wet cake was washed with purified water (3 x 5 Vol), followed by methanol (5 Vol). The cake was vacuum dried for 3 h. then the wet cake and dimethyl sulfoxide (20 Vol) were charged into a reactor. The mass was heated to 120-125 C to get clear solution then the mass was cooled to ambient temperature and stirred for 2 h, then filtered. The wet cake was washed with methanol (3x 4.0 Vol) and vacuum dried for 2 h. The wet cake was dried in VTD at below 55C under vacuum
  • 3
  • 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
  • [ 5744-80-9 ]
  • 3-amino-5-(dicyclopropylmethyl)-7-(1,5-dimethyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
104 mg Example 173 3-amino-5-(dicyclopropylmethyl)-7-(1,5-dimethyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (0879) A mixture of 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one (300 mg) obtained in Example 78, Step C, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (283 mg), tetrakis(triphenylphosphine)palladium(0) (107 mg), potassium acetate (182 mg) and N,N-dimethylacetamide (4 mL) was stirred under an argon atmosphere at 110C for 4 hr. The reaction mixture was cooled to room temperature, <strong>[5744-80-9]3-bromo-1,5-dimethyl-1H-pyrazole</strong> (195 mg), aqueous sodium carbonate solution (2 M, 0.928 mL) and tetrakis(triphenylphosphine)palladium(0) (107 mg) were added. Under an argon atmosphere, the reaction mixture was stirred at 130C for 5 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate) and further purified by silica gel chromatography (diol silica gel, hexane/ethyl acetate). The obtained solid was crystallized from ethyl acetate/diisopropyl ether to give the title compound (104 mg).
  • 4
  • [ 138091-52-8 ]
  • [ 5744-80-9 ]
  • tert-butyl 3-(1,5-dimethylpyrazol-3-yl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 120℃; for 19h;Inert atmosphere; The title compound was obtained in analogy to example 48, intermediate a, from tert-butyl 4- oxo- 1 -phenyl- 1,3 ,8-triazaspiro [4. 5]decane-8-carboxylate (example 35, intermediate c) and 3- bromo-1,5-dimethyl-1H-pyrazole (CAS RN 5744-80-9) at 120C over 19 hours as a colorlesssolid. MS (ESI): mlz = 426.25 [M+H]; To a suspension of tert-butyl 4-oxo- 1 -phenyl- 1,3, 8-triazaspiro [4.51 decane- 8-carboxylate (100 mg, 302 imol, example 35, intermediate c) and 1-ethyl-3-iodo-1H-pyrazole (67 mg, 302 imol, CAS RN 120278 1-34-7) in dioxane (2 mL) were added K2C03 (125 mg, 905 imol), DMEDA(6.11 iL, 48.3 imol, CAS RN 110-70-3) and Cul (4.6 mg, 24.1 imol) and the mixture was purged with argon. The suspension was heated to 100C and stuffed at this temperature over 14 hours. The reaction mixture was filtered over a microfilter, the filtrate was washed with a small volume of EtOAc and MeOH, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 4 g column using an MPLC (ISCO) system elutingwith a gradient of n-heptane : EtOAc (100: 0 to 50: 50) to give the title compound as a colorless solid (0.107 g; 83.3%).
  • 5
  • 1,5-dimethylpyrazolidin-3-one hydrobromide [ No CAS ]
  • [ 5744-80-9 ]
  • 6
  • 1,5-dimethylpyrazolidin-3-one hydrobromide [ No CAS ]
  • C8H12Br2N4 [ No CAS ]
  • [ 5744-80-9 ]
  • 7
  • 3-bromo-1,5-dimethyl-4,5-dihydro-1H-pyrazole [ No CAS ]
  • [ 5744-80-9 ]
  • 8
  • 3-bromo-1,5-dimethyl-4,5-dihydro-1H-pyrazole [ No CAS ]
  • C8H12Br2N4 [ No CAS ]
  • [ 5744-80-9 ]
  • 9
  • 1,5-dimethylpyrazolidin-3-one hydrobromide [ No CAS ]
  • [ 57097-81-1 ]
  • [ 5744-80-9 ]
  • 10
  • 3-bromo-1,5-dimethyl-4,5-dihydro-1H-pyrazole [ No CAS ]
  • [ 57097-81-1 ]
  • [ 5744-80-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: Add N-methyl-3,5-dibromopyrazole (1 g) and 15 ml of THF to a 50 mL three-necked flask. Under a nitrogen atmosphere, the temperature was lowered to -78 C, and n-BuLi (1.83 ml) was slowly added. The reaction was carried out at -78 C for 0.5 h.Then, acetone (0.398 ml) was added at -78 C, and the reaction was completed at -78 C for 30 min, and then slowly stirred to room temperature and stirred for 10 h.The reaction was completed, quenched, extracted with water and ethyl acetate twice, and the organic layer was combined, dried over anhydrous Na2SO?2-(1-Methyl-3-bromo-1H-pyrazol-5-yl)-2-propanol.
  • 12
  • (S)-tert-butyl 3-((4-(2-((5-amino-2-methylnaphthalen-1-yl)oxy)pyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate [ No CAS ]
  • [ 5744-80-9 ]
  • (S)-tert-butyl 3-((4-(2-((5-((1,5-dimethyl-1H-pyrazol-3-yl)amino)-2-methylnaphthalen-1-yl)oxy)pyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2?,4?,6?-triisopropyl-1,1?-biphenyl)-2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate; sodium hydride; In 1,4-dioxane; at 120℃; for 12h;Inert atmosphere; To a solution of tert-butyl (3S)-3- [[4- [2- [(5 -amino-2-methyl- 1 -naphthyl)oxy]-3 - pyridyl]pyrimidin-2-yl] amino]piperidine- 1 -carboxylate (100 mg, 0.19 mmol), 3 -bromo- 1,5 - dimethyl-pyrazole (50 mg, 0.28 mmol), 2-methylpropan-2-olate; sodium hydride (46 mg, 0.47 mmol) in 1 ,4-dioxane were added [2-(2-aminophenyl)phenyl]-methylsulfonyloxy-palladium; dicyclohexyl- [3 ,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (17 mg, 0.02 mmol), 2-(dicyclohexylphosphino)3 ,6-dimethoxy-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl (20 mg, 0.04 mmol) under nitrogen atmosphere. The mixture was stirred at 120 C for 12 h. The solution was concentrated and purified by prep-TLC (50% ethyl acetate in petroleum ether, Rf= 0.4) to yield 50 mg (42% yield) of the title compound as a white solid.
  • 13
  • N-(3-((4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl)acrylamide [ No CAS ]
  • [ 5744-80-9 ]
  • N-[3-((4-amino-3-(1,5-dimethyl-1H-3-pyrazolyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)phenyl]-2-propenamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.
  • 14
  • 1-[3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-pyrrolidinyl]-2-propen-1-one [ No CAS ]
  • [ 5744-80-9 ]
  • 1-(3-(4-amino-3-(1,5-dimethyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.
  • 15
  • 1-[3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinyl]-2-propen-1-one [ No CAS ]
  • [ 5744-80-9 ]
  • 1-(3-(4-amino-3-(1,5-dimethyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.
  • 16
  • 1-[4-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinyl]-2-propen-1-one [ No CAS ]
  • [ 5744-80-9 ]
  • 1-(4-(4-amino-3-(1,5-dimethyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.
  • 17
  • 1-[4-((4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-1-piperidinyl]-2-propene-1-one [ No CAS ]
  • [ 5744-80-9 ]
  • 1-(4-((4-amino-3-(1,5-dimethyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d] pyrimidin-1-yl)methyl)piperidin-1-yl)prop-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.
  • 18
  • 1-(3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-2-(dimethylamino)ethanone [ No CAS ]
  • [ 5744-80-9 ]
  • 1-(3-(4-amino-3-(1,5-dimethyl-1H-pyrazol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-2-(dimethylamino)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [M+H]+.
  • 19
  • [ 1361019-05-7 ]
  • [ 74-88-4 ]
  • [ 5744-80-9 ]
YieldReaction ConditionsOperation in experiment
88% To a solution of 23 (11.9 g, 50 mmol) in THF (150 mL) was added n-BuLi (22 mL, 55 mmol, 2.5M in hexane) at -78 C. After being stirred at -78 C for 0.5 h under argon, iodomethane (8.9 g, 62.5 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 10 h under argon. To the mixture was added H2O, and extraction was done twice with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (EtOAc/hexane=0:10 to 1:2) to give 19c(7.7 g, 88%) as a pale yellow oil. MS (ESI) m/z: 174.8 [M+H]+.
  • 20
  • 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole [ No CAS ]
  • [ 52409-22-0 ]
  • [ 5744-80-9 ]
  • C37H42BrN6PPd [ No CAS ]
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