5744-80-9|3-Bromo-1,5-dimethyl-1H-pyrazole| Ambeed

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Quality Control of [ 5744-80-9 ] Purity: 97% SDS Specification

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Product Details of [ 5744-80-9 ]

CAS No. :	5744-80-9
Formula :	C₅H₇BrN₂
M.W :	175.03
SMILES Code :	CC1=CC(Br)=NN1C
MDL No. :	MFCD09991542
InChI Key :	NELVNOMSYNLQGQ-UHFFFAOYSA-N
Pubchem ID :	21724046

Safety of [ 5744-80-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 5744-80-9 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.84
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.66
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.49
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.17
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.48
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.53

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.43
Solubility	0.645 mg/ml ; 0.00369 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.65
Solubility	3.94 mg/ml ; 0.0225 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.03
Solubility	1.62 mg/ml ; 0.00927 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.19 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.71

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.

Upstream synthesis route of [ 5744-80-9 ]
Downstream synthetic route of [ 5744-80-9 ]

[ 5744-80-9 ] Synthesis Path-Upstream 1~1

1
[ 1361019-05-7 ]
[ 74-88-4 ]
[ 5744-80-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; for 10 h; Inert atmosphere	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, 88percent) as a pale yellow oil. MS (ESI) m/z: 174.8 [M+H]+.

References: [1] Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 8, p. 1562 - 1576.

[ 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 ]

Yield	Reaction Conditions	Operation 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%)

References: [1]Patent: WO2015/31562,2015,A1 .Location in patent: Page/Page column 32; 33.

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 ]

Yield	Reaction Conditions	Operation 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

References: [1]Patent: WO2015/31562,2015,A1 .Location in patent: Page/Page column 31.

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 ]

Yield	Reaction Conditions	Operation 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).

References: [1]Patent: EP2980089,2016,A1 .Location in patent: Paragraph 0879.

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 ]

Yield	Reaction Conditions	Operation 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%).

References: [1]Patent: WO2017/5583,2017,A1 .Location in patent: Page/Page column 89; 91.

5
1,5-dimethylpyrazolidin-3-one hydrobromide [ No CAS ]
[ 5744-80-9 ]

References: [1]Organic Process Research and Development,2017,vol. 21,p. 754 - 762.

6
1,5-dimethylpyrazolidin-3-one hydrobromide [ No CAS ]
C₈H₁₂Br₂N₄ [ No CAS ]
[ 5744-80-9 ]

References: [1]Organic Process Research and Development,2017,vol. 21,p. 754 - 762.

7
3-bromo-1,5-dimethyl-4,5-dihydro-1H-pyrazole [ No CAS ]
[ 5744-80-9 ]

References: [1]Organic Process Research and Development,2017,vol. 21,p. 754 - 762.

8
3-bromo-1,5-dimethyl-4,5-dihydro-1H-pyrazole [ No CAS ]
C₈H₁₂Br₂N₄ [ No CAS ]
[ 5744-80-9 ]

References: [1]Organic Process Research and Development,2017,vol. 21,p. 754 - 762.

9
1,5-dimethylpyrazolidin-3-one hydrobromide [ No CAS ]
[ 57097-81-1 ]
[ 5744-80-9 ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 2830 - 2839.

10
3-bromo-1,5-dimethyl-4,5-dihydro-1H-pyrazole [ No CAS ]
[ 57097-81-1 ]
[ 5744-80-9 ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 2830 - 2839.

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Patent: WO2018/166528,2018,A1 .Location in patent: Paragraph 0899; 0900.

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 ]

Yield	Reaction Conditions	Operation 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]+.