[ CAS No. 869973-96-6 ] {[proInfo.proName]}

Name: 869973-96-6|(1-Methyl-1H-pyrazol-3-yl)boronic acid|97%
Brand: Ambeed
SKU: A222528
Rating: 96 (27 reviews)

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Quality Control of [ 869973-96-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 869973-96-6 ]

Product Details of [ 869973-96-6 ]

CAS No. :	869973-96-6	MDL No. :	MFCD11977279
Formula :	C₄H₇BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WUDMJZRGWGQBQH-UHFFFAOYSA-N
M.W :	125.92	Pubchem ID :	53338706
Synonyms :

Calculated chemistry of [ 869973-96-6 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	33.31
TPSA :	58.28 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.83
Log Po/w (WLOGP) :	-1.9
Log Po/w (MLOGP) :	-1.79
Log Po/w (SILICOS-IT) :	-2.09
Consensus Log Po/w :	-1.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.44
Solubility :	45.4 mg/ml ; 0.361 mol/l
Class :	Very soluble
Log S (Ali) :	0.09
Solubility :	154.0 mg/ml ; 1.22 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.35
Solubility :	285.0 mg/ml ; 2.26 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.01

Safety of [ 869973-96-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 869973-96-6 ]

* 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 [ 869973-96-6 ]

[ 869973-96-6 ] Synthesis Path-Downstream 1~17

1
[ 869973-96-6 ]
C₄₁H₄₀ClFN₂O₈ [ No CAS ]
C₄₅H₄₅FN₄O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5809 - 5814

2
[ 869973-96-6 ]
[ 591-19-5 ]
3-(1-methyl-1H-pyrazol-3-yl)aniline [ No CAS ]

Reference： [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 5942 - 5947,6

3
[ 869973-96-6 ]
C₁₃H₈Br₂N₂O₂S [ No CAS ]
C₁₇H₁₃BrN₄O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4344 - 4353

4
[ 15864-32-1 ]
[ 869973-96-6 ]
C₁₁H₁₀N₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3189 - 3193

5
[ 869973-96-6 ]
tert-butyl (3-bromo-5-methylpyrazolo[1,5-a]pyrimidin-7-yl)(pyridin-2-ylmethyl)carbamate [ No CAS ]
5-methyl-3-(1-methyl-1H-pyrazol-3-yl)-N-(pyridin-2-ylmethyl)pyrazolo[1,5-a]pyrimidin-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		General procedure: To a solution of 12 (1 equiv) in dioxane and water (5:1) was added boronic acid (1.2 equiv) followed by addition of cesium carbonate (1 equiv) and PdCl2(dffp) (0.1 equiv). The reaction mixture was degassed and heated at 80C overnight. The reaction was diluted with EtOAc and washed with water (2). After drying over Na2SO4, filtration and concentration, the crude product was dissolved in DCM (4 ml) and TFA (8 ml) was added. The reaction was stirred for 4 h at rt followed by concentration. The residue was dissolved in DCM and washed with 10% Na2CO3 (2), the organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by flash column chromatography (80% EtOAc/Hex) or recrystallization from DCM/Hexane or by prep TLC (EtOAc) to give the desired product

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7240 - 7250

6
[ 869973-96-6 ]
3-bromo-4-[3-methyl-2,5-dioxo-1-(2-trifluoromethylpyridin-4-yl)-2,3,4,5,6,7-hexahydro-1H-cyclopentapyrimidin-4-yl]benzonitrile [ No CAS ]
C₂₅H₁₉F₃N₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In N,N-dimethyl-formamide; at 150℃; for 0.666667h;Inert atmosphere; Microwave irradiation;	3-Bromo-4-[3-methyl-2,5-dioxo-1-(2-trifluoromethyl-pyridin-4-yl)-2,3,4,5,6,7-hexahydro-1H-cyclopentapyrimidin-4-yl]-benzonitrile (intermediate 23)(61.4 mg, 0.1 mmol) and furan-3-yl-boronic acid (16.8 mg, 0.15 mmol) are suspended in N,N-dimethylformamide (2 mL) and are degassed with a stream of argon gas argon. 1,1?-bis(di-tert-butylphosphino)-ferrocene-palladium dichloride, complex with dichloromethane (1:1) (1.3 mg, 0.002 mmol) and cesium carbonate solution (2 mol/L, 100 muL, 0.20 mmol) are added and the mixture is stirred at 100 C. overnight. The mixture is filtered over a short column of PR18 silica gel/basic aluminum oxide. Purification is performed by reversed phase HPLC. Yield: 19.6 mg; ESI mass spectrum [M+H]+=479; Retention time HPLC: 0.69 min (method X018_S01). (0400) The following examples of Table 10 are prepared in analogy of 3-Furan-3-yl-4-[3-methyl-2,5-dioxo-1-(2-trifluoromethyl-pyridin-4-yl)-2,3,4,5,6,7-hexahydro-1H-cyclopentapyrimidin-4-yl]-benzonitrile (example 17), using the appropriate boronic acids or boronic acid esters as starting material. Examples 17.2 and 17.3 are synthesized using acetonitrile as solvent and potassium carbonate as base. Examples 17.1, 17.2 and 17.3 are synthesized under microwave irradiation for 40 min at 150 C.

Reference： [1]Patent: US2016/31830,2016,A1 .Location in patent: Paragraph 0400

7
[ 869973-96-6 ]
7-((6-bromo-3-fluoropyridin-2-yl)methoxy)-N,3-ditrityl-3H-[1,2,3]triazolo[4,5-b]pyridin-5-amine [ No CAS ]
7-((3-fluoro-6-(1-methyl-iH-pyrazol-3-yl)pyridin-2-yl)methoxy)-3H-[1,2,3]triazolo[4,5-b]pyridin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.9 mg		[00342j To a vial with a septum cap were added Example 95A (50 mg, 0.061 mmol), (i-methyl-1H-pyrazol-3-yl)boronic acid (8 mg, 0.061 mmol), K2C03 (17 mg, 0.12mmol), and tetrakis(triphenylphosphine)palladium(0) (7 mg, 6.1 jimol). The vial was evacuated and back-filled with argon three times. Degassed DMF (2.7 mL) and water (0.3 mL) were added. The reaction mixture was stirred at 90 C for 1.5 h. The crude reaction was then diluted with DCM (4 mL), filtered, and used as such in the next reaction. To the above solution was added TFA (1 mL) to produce a bright yellow solution. After 1 minute, triethylsilane (20 jiL, 120 mmol) was added and the reactionmixture was concentrated in vacuo. The crude product was purified by prep HPLC to yield Example 96 (1.9 mg, 9% yield over 2 steps). MS (ESI) m/z 341 (M+H). 1H NMR (500 MHz, DMSO-d6) oe 7.99 - 7.89 (m, 2H), 7.46 (d, J = 1.7 Hz, 1H), 6.81 (d, J = 1.7 Hz, 1H), 6.15 (br. s., 1H), 5.67 (s, 2H), 3.95 (s, 3H).

Reference： [1]Patent: WO2016/40417,2016,A1 .Location in patent: Paragraph 00342

8
[ 869973-96-6 ]
ethyl 10'-bromo-9'-(cyclopropylmethoxy)-2'-oxo-2',7'-dihydrospiro[cyclobutane-1,6'-pyrido[2,1-a]isoquinoline]-3'-carboxylate [ No CAS ]
ethyl 9'-(cyclopropylmethoxy)-10'-(1-methyl-1H-pyrazol-3-yl)-2'-oxo-2',7'-dihydrospiro[cyclobutane-1,6'-pyrido[2,1-a]isoquinoline]-3'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		To a stirred solution of ethyl 1 0'-bromo-9'-(cyclopropylmethoxy)-2'-oxo-2', 7'-d ihyd rospiro[ cyclobutane-1 ,6'-pyrido[2, 1-a]isoqu inoline ]-3 '-carboxylate (1 00 mg,0.21 mmol) in DME (2 ml) and water (0.5 ml) were added Na2C03 (44 mg, 0.42 mmol) andPd(dppf)Cb (8 mg, 0.011 mmol), and the reaction mixture was stirred for 30 min at r.t underAr. (1-methyl-1 H-pyrazol-3-yl)boronic acid (52 mg, 0.42 mmol) was then added and thereaction mixture was stirred for 12 hr at reflux. The reaction was quenched at room temperature by addition of deionized H20. The solution was extracted with EtOAc and thecombined organic layer was dried over MgS04, filtered, and concentrated in vacuo. Silicagel chromatography afforded the title compound (50 mg, 49% yield) as a white solid. LCMS(ESI) m/z: 460.4 (M + 1t.

Reference： [1]Patent: WO2018/154466,2018,A1 .Location in patent: Paragraph 00980; 00982; 00983

9
[ 869973-96-6 ]
6-chloro-5-(quinolin-6-yl)pyrazin-2-amine [ No CAS ]
6-(1-methyl-1H-pyrazol-3-yl)-5-(quinolin-6-yl)pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 100℃; for 18h;Inert atmosphere;	To a stirred solution of 6-chloro-5-(quinolin-6-yl)pyrazin-2-amine (150 mg, 0.58 mmol, 1.0 eq.) and <strong>[869973-96-6](1-methyl-1H-pyrazol-3-yl)boronic acid</strong> (81 mg, 0.64 mmol, 1.1 eq.) in dioxane (5 mL) and water (1 mL), was added Na2CO3 (122 mg, 1.16 mmol, 2.0 eq.). The reaction was purged with N2 for 5 min. To this reaction mixture was added Pd(dppf)Cl2'DCM complex (24 mg, 5 mol %) and N2 was purged again for another 5 min. The reaction mixture was heated at 100 C. for 18 h. progress of reaction was monitored by TLC and LCMS On completion of the reaction, the reaction mixture was extracted with ethyl acetate (35 mL3). Combined organic layer was washed with water (50 mL2), dried over anhydrous Na2SO4 and concentrated under vacuum to get the solid residue which was purified by reversed phase column chromatography to afford the desired product 6-(1-methyl-1H-pyrazol-3-yl)-5-(quinolin-6-yl)pyrazin-2-amine (14 mg, 9%) as an off white solid. LCMS: 303 [M+1]+. 1H NMR: (400 MHz, DMSO-d6) delta 8.85 (d, J=2.63 Hz, 1H), 8.30 (d, J=7.89 Hz, 1H), 7.92-8.03 (m, 2H), 7.84 (d, J=8.77 Hz, 1H), 7.55-7.64 (m, 2H), 7.49 (dd, J=4.39, 8.33 Hz, 1H), 6.65 (s, 2H), 6.12 (d, J=2.19 Hz, 1H), 3.71 (s, 3H).

Reference： [1]Patent: US2019/23666,2019,A1 .Location in patent: Paragraph 0542; 0543; 0544

10
[ 869973-96-6 ]
(S)-4-chloro-6-(3-fluoropyrrolidin-1-yl)-N-(6-isopropylpyridin-3-yl)pyrimidine-5-carboxamide [ No CAS ]
C₂₁H₂₄FN₇O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2,2-diphenyl-1-methylcyclopropyl)phosphine; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; at 120℃; for 1h;Microwave irradiation;	General procedure: Amixture of (S)-4-chloro-6-(3-fluoropyrrolidin-1-yl)-N-(6-isopropylpyridin-3-yl)pyrimidine-5-carboxamide(Step 2 for 14) (0.0291 g, 0.0800 mmol) , (2,5-difluorophenyl)boronic acid (37.9mg, 0.240 mmol), Pd2(dba)3 (2.93 mg, 0.0320 mmol),dicyclohexyl(1-methyl-2,2-diphenylcyclopropyl)phosphine (12.9 mg, 0.0320 mmol)and K3PO4 (50.9 mg, 0.240 mmol) in DME (1 mL) and anhydrous DMF (0.2 mL) in asealed was stirred at 120 C under microwave irradiation (Biotage Initiator) for1 h. The reaction mixture was poured into EtOAc (6 mL) and water (2 mL), andstirred for 5 min. The insoluble material was removed by filtration, theorganic layer was separated and the organic solvent was removed by blowing awaywith the air at 60 C. The residue was purified by preparative HPLC (YMC Triart C18, eluted with MeCN/10 mM aqueousNH4HCO3 solution).The desired fraction was concentratedby blowing away with the air at 60 C to give 4-(2,5-difluorophenyl)-6-((3S)-3-fluoropyrrolidin-1-yl)-N-(6-isopropylpyridin-3-yl)pyrimidine-5-carboxamide(18) (16.8 mg, 48%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 815 - 820

11
[ 151049-87-5 ]
[ 73183-34-3 ]
[ 869973-96-6 ]

Yield	Reaction Conditions	Operation in experiment
89.28%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 16h;	Step-1: Synthesis of (1-methyl-1H-pyrazol-3-yl)boronic acid To a stirred solution of 3-bromo-1-methyl-1H-pyrazole (10 g, 62.11 mmol, 1 eq.) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (23.6 g, 93.167 mmol, 1.5 eq.) in 120 mL of dioxane was added potassium acetate (18.28 g, 186.33 mmol, 3.0 eq.). The reaction mixture was purged with N2 for about 5 min and Pd(dppf)Cl2.DCM complex (2.5 g, 3.105 mmol, 0.05 eq.) was added. The reaction mixture was re-purged with N2 and heated at 100 C. for 16 h. Following this reaction mixture was allowed to cool to rt and filtered through celite bed and washed with ethyl acetate (200 mL). The obtained organic layer was concentrated under reduced pressure to get desired product, (1-methyl-1H-pyrazol-3-yl)boronic acid (6.5 g, 89.28%) as an off white solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 1002-1004

12
[ 955368-93-1 ]
[ 869973-96-6 ]
2-isopropyl-1-(1-methyl-1H-pyrazol-3-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.6%	With [2,2]bipyridinyl; copper diacetate; sodium carbonate; In dichloromethane; at 20℃; for 24h;	Step-2: Synthesis of 2-isopropyl-1-(1-methyl-1H-pyrazol-3-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one To a stirred solution of 2-isopropyl-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (300 mg, 1.337 mmol, 1 eq.) and <strong>[869973-96-6](1-methyl-1H-pyrazol-3-yl)boronic acid</strong> (340 mg, 2.675 mmol, 2.0 eq) in DCM (10 mL) was added 2,2-bipyridine (417 mg, 2.675 mmol, 2.0 eq.), copper acetate (474 mg, 2.675 mmol, 2.0 eq.) and Na2CO3 (425 mg, 4.012 mmol, 3.0 eq). The reaction mixture was stirred at rt for 24 h in open air. The progress of reaction was monitored by TLC. The reaction mass was diluted with water (200 mL) and extracted with ethyl acetate (200 mL*2) and the organic layer was dried over Na2SO4, concentrated and purified by column chromatography (Combiflash, Elution: 0-30% EtOAc in Hexane) to afford the desired product, 2-isopropyl-1-(1-methyl-1H-pyrazol-3-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (100 mg, 24.6%) as brown solid.

Reference： [1]Patent: US2019/106427,2019,A1 .Location in patent: Paragraph 1002; 1005; 1006

13
[ 869973-96-6 ]
N-(6-bromo-1H-indazol-3-yl)-4-(4-ethylpiperazin-1-yl)benzamide [ No CAS ]
4-(4-ethylpiperazin-1-yl)-N-(6-(1-methyl-1H-pyrazol-3-yl)-1H-indazol-3-yl)benzamide [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2020,vol. 35,p. 72 - 84

14
[ 869973-96-6 ]
3-[(5-bromopyridin-3-yl)methylamino]-4-fluoro-N-[3-(trifluoromethoxy)phenyl]benzamide [ No CAS ]
4-fluoro-3-[(5-(1-methyl-1H-pyrazol-3-yl)pyridin-3-yl)methylamino]-N-[3(trifluoromethoxy)phenyl]benzamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019

15
[ 869973-96-6 ]
3-(((5-bromopyridin-3-yl)methyl)amino)-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide [ No CAS ]
4-methyl-3-(((5-(1-methyl-1H-pyrazol-3-yl)pyridin-3-yl)methyl)amino)-N-(3(trifluoromethyl)phenyl) benzamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019

16
[ 869973-96-6 ]
4-(5-chloropyridin-3-yl)benzamide [ No CAS ]
4-[5-(1-methyl-1H-pyrazol-3-yl)pyridin-3-yl]benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020

17
[ 869973-96-6 ]
ethyl 4-(4-bromobenzyl)pyrrolo[1,2-b]pyridazine-2-carboxylate [ No CAS ]
ethyl 4-[4-(1-methyl-1H-pyrazol-4-yl)-benzyl]pyrrolo[1,2-b]pyridazine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With dichloro bis((p-dimethylaminophenyl)-?-di-tert-butylphosphine)palladium(II); potassium acetate; In 1,4-dioxane; water; at 100℃; for 5h;Inert atmosphere; Sealed tube;	To a stirred solution ofethyl 4-(4-bromobenzyl)-pyrrolo[l,2-h]pyridazine-2- carboxylate as obtained in step-2 (1.28 g, 3.57mmol) in a mixture of l,4-dioxan (35.7 mL) and water (7.1 mL), potassium acetate (0.88 g, 8.92 mmol), <strong>[869973-96-6]N-methylpyrazoleboronic acid</strong> (0.58 g, 4.64 mmol) were added. The reaction mass was degassed for 15 minutes. The Bis(di- ier/-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Pd(amphos)2Cl2)(0.25 g, 0.36 mmol) was added and the screw cap was tightened on the seal tube. The contents were heated to 100 C for 5 h. The reaction mass was cooled to RT, diluted with EtOAc, washed with water followed by brine solution. The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure to obtain a crude mass which was purified by silica gel column chromatography which afforded the title compound (ethyl 4-[4- (l-methyl-lH-pyrazol-4-yl)-benzyl]-pyrrolo[l,2-h]pyridazine-2-carboxylate) (0.91 g) in 71% yield. 1H - NMR (400 MHz, CDCl3):5 7.90 (s, 1H), 7.73 (s, 1H), 7.59 (s, 1H), 7.42 (d, J - 8.0 Hz, 2H), 7.28 (d, J - 8.0 Hz, 2H), 7.05 (s, 1H), 6.96 (dd, J = 2.8, 4.0 Hz, 1H), 6.21 (d, J = 4.0 Hz, 1H), 4.48 (q, 2H), 4.16 (s, 2H), 3.93 (s, 3H), 1.43 (t, J = 6.8 Hz, 3H);Mass (m/z); 361.0 (M+H)+.

Reference： [1]Patent: WO2020/79606,2020,A1 .Location in patent: Page/Page column 29-30

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