[ CAS No. 1211516-09-4 ] {[proInfo.proName]}

Name: 1211516-09-4|6-Bromo-1H-pyrazolo[4,3-b]pyridin-3-amine|97%
Brand: Ambeed
SKU: A201146
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3d Animation Molecule Structure of 1211516-09-4

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Quality Control of [ 1211516-09-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1211516-09-4 ]

SDS Specification

Alternatived Products of [ 1211516-09-4 ]

Product Details of [ 1211516-09-4 ]

CAS No. :	1211516-09-4	MDL No. :	MFCD08062675
Formula :	C₆H₅BrN₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GORWCQUHVRKSTN-UHFFFAOYSA-N
M.W :	213.04	Pubchem ID :	50989712
Synonyms :

Calculated chemistry of [ 1211516-09-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.99
TPSA :	67.59 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.8
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.77
Log Po/w (SILICOS-IT) :	1.53
Consensus Log Po/w :	1.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.34
Solubility :	0.975 mg/ml ; 0.00458 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	2.59 mg/ml ; 0.0122 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.04
Solubility :	0.195 mg/ml ; 0.000914 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.96

Safety of [ 1211516-09-4 ]

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

Application In Synthesis of [ 1211516-09-4 ]

* 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 [ 1211516-09-4 ]

[ 1211516-09-4 ] Synthesis Path-Downstream 1~11

1
[ 1211516-09-4 ]
[ 2412024-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dmap / acetonitrile / 12 h / Reflux 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.2: 1 h / 25 °C
	Multi-step reaction with 3 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C

Reference： [1]Current Patent Assignee: ARCUS BIOSCIENCES INC - WO2020/46813, 2020, A1
[2]Beatty, Joel W.; Lindsey, Erick A.; Thomas-Tran, Rhiannon; Debien, Laurent; Mandal, Debashis; Jeffrey, Jenna L.; Tran, Anh T.; Fournier, Jeremy; Jacob, Steven D.; Yan, Xuelei; Drew, Samuel L.; Ginn, Elaine; Chen, Ada; Pham, Amber T.; Zhao, Sharon; Jin, Lixia; Young, Stephen W.; Walker, Nigel P.; Leleti, Manmohan Reddy; Moschütz, Susanne; Sträter, Norbert; Powers, Jay P.; Lawson, Kenneth V. [Journal of Medicinal Chemistry, 2020, vol. 63, # 8, p. 3935 - 3955]

2
[ 1211516-09-4 ]
[ 2412024-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: dmap / acetonitrile / 12 h / Reflux 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.2: 1 h / 25 °C 3.1: 2 h / 120 °C / Sealed tube

Reference： [1]Current Patent Assignee: ARCUS BIOSCIENCES INC - WO2020/46813, 2020, A1

3
[ 1211516-09-4 ]
[ 2412024-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: dmap / acetonitrile / 12 h / Reflux 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.2: 1 h / 25 °C 3.1: 2 h / 120 °C / Sealed tube 4.1: ethanol / 1.5 h / 80 °C / Sealed tube 4.2: 1 h / 80 °C
	Multi-step reaction with 6 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C 4: 2 h / 100 °C / Sealed tube 5: ethanol / 1.5 h / 80 °C / Sealed tube 6: hydrogenchloride / 1,4-dioxane / 1 h / 80 °C

4
[ 1211516-09-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: dmap / acetonitrile / 12 h / Reflux 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.2: 1 h / 25 °C 3.1: 2 h / 120 °C / Sealed tube 4.1: ethanol / 1.5 h / 80 °C / Sealed tube 4.2: 1 h / 80 °C 5.1: N,N`-dimethylethylenediamine; potassium phosphate; copper(l) iodide / N,N-dimethyl-formamide / 20 h / 135 °C / Inert atmosphere; Sealed tube 5.2: 1 h / 45 °C

Reference： [1]Current Patent Assignee: ARCUS BIOSCIENCES INC - WO2020/46813, 2020, A1

5
[ 24424-99-5 ]
[ 1211516-09-4 ]
[ 2412024-85-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap In acetonitrile for 12h; Reflux;
12 g	With dmap In acetonitrile for 12h; Reflux;	38.a Step a To a solution of 6-bromo-l//-pyrazolo[4,3-b]pyridin-3-amine (5.04 g, 23.6 mmol, 1.0 equiv) in CH3CN (1 18 mL) was added B0C2O (25.8 g, 118 mmol, 5.0 equiv), followed by DMAP (144 mg, 1.18 mmol, 5 mol%). The resulting mixture was stirred at reflux for 12 h. Upon completion, the reaction mixture was cooled to 25 °C, concentrated under reduced pressure, and purified by column chromatography (S1O2, CEhCh/EtOAc) to afford /er/-butyl 3- (bis( er -butoxycarbonyl)amino)-6-bromo- 1 /-pyrazolo[4,3-h]pyridinc- 1 -carboxylatc (12.0 g) as a white solid.

Reference： [1]Beatty, Joel W.; Lindsey, Erick A.; Thomas-Tran, Rhiannon; Debien, Laurent; Mandal, Debashis; Jeffrey, Jenna L.; Tran, Anh T.; Fournier, Jeremy; Jacob, Steven D.; Yan, Xuelei; Drew, Samuel L.; Ginn, Elaine; Chen, Ada; Pham, Amber T.; Zhao, Sharon; Jin, Lixia; Young, Stephen W.; Walker, Nigel P.; Leleti, Manmohan Reddy; Moschütz, Susanne; Sträter, Norbert; Powers, Jay P.; Lawson, Kenneth V. [Journal of Medicinal Chemistry, 2020, vol. 63, # 8, p. 3935 - 3955]
[2]Current Patent Assignee: ARCUS BIOSCIENCES INC - WO2020/46813, 2020, A1 Location in patent: Paragraph 0234

6
[ 1211516-09-4 ]
[ 2412024-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere

7
[ 1211516-09-4 ]
[ 2582815-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C 4: 2 h / 100 °C / Sealed tube

8
[ 1211516-09-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C 4: 2 h / 100 °C / Sealed tube 5: ethanol / 1.5 h / 80 °C / Sealed tube

9
[ 1211516-09-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C 4: 2 h / 100 °C / Sealed tube 5: ethanol / 1.5 h / 80 °C / Sealed tube 6: hydrogenchloride / 1,4-dioxane / 1 h / 80 °C 7: copper(l) iodide; N,N`-dimethylethylenediamine; potassium phosphate / N,N-dimethyl-formamide / 20 h / 135 °C / Inert atmosphere; Sealed tube

10
[ 1211516-09-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C 4: 2 h / 100 °C / Sealed tube 5: ethanol / 1.5 h / 80 °C / Sealed tube 6: hydrogenchloride / 1,4-dioxane / 1 h / 80 °C 7: copper(l) iodide; N,N`-dimethylethylenediamine; potassium phosphate / N,N-dimethyl-formamide / 20 h / 135 °C / Inert atmosphere; Sealed tube 8: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 45 °C 9: acetonitrile; water

11
[ 1211516-09-4 ]
[ 2412020-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: dmap / acetonitrile / 12 h / Reflux 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 3: sodium periodate; potassium osmate(VI) dihydrate; 2,6-dimethylpyridine / tetrahydrofuran; water / 1 h / 25 °C 4: 2 h / 100 °C / Sealed tube 5: ethanol / 1.5 h / 80 °C / Sealed tube 6: hydrogenchloride / 1,4-dioxane / 1 h / 80 °C 7: copper(l) iodide; N,N`-dimethylethylenediamine; potassium phosphate / N,N-dimethyl-formamide / 20 h / 135 °C / Inert atmosphere; Sealed tube 8: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 45 °C

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1211516-09-4 ] {[proInfo.proName]}

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[ 1211516-09-4 ] Synthesis Path-Downstream 1~11

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Amines

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