[ CAS No. 53902-76-4 ]

Name: 53902-76-4|Pyrazolo[1,5-a]pyrazine-3-carboxylic acid|95%
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Quality Control of [ 53902-76-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53902-76-4 ]

Product Details of [ 53902-76-4 ]

CAS No. :	53902-76-4	MDL No. :	MFCD11865260
Formula :	C₇H₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KDZOHLVVUNZUQC-UHFFFAOYSA-N
M.W :	163.13 g/mol	Pubchem ID :	67123720
Synonyms :

Calculated chemistry of [ 53902-76-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.95
TPSA :	67.49 Å²

Pharmacokinetics

GI absorption :	High
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) :	-7.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.84
Log Po/w (XLOGP3) :	-0.48
Log Po/w (WLOGP) :	0.43
Log Po/w (MLOGP) :	-0.17
Log Po/w (SILICOS-IT) :	-0.19
Consensus Log Po/w :	0.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.04
Solubility :	14.9 mg/ml ; 0.0916 mol/l
Class :	Very soluble
Log S (Ali) :	-0.47
Solubility :	55.2 mg/ml ; 0.339 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.08
Solubility :	13.7 mg/ml ; 0.0838 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 53902-76-4 ]

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 [ 53902-76-4 ]

* 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 [ 53902-76-4 ]

[ 53902-76-4 ] Synthesis Path-Downstream 1~15

Yield	Reaction Conditions	Operation in experiment
99%
	/BRN= 611546/ (VI), c. HCl, Δ (neben /BRN= 606567/ (XIX));

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[ 53902-76-4 ]
pyrazolo[1,5-a]pyrazine-3-carboxylic acid chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride for 1h; Reflux;
	With thionyl chloride for 4h; Reflux;	3 3) Preparation of the compound of example 7:; A suspension of pyrazolo[1 ,5-a]pyrazine-3-carboxylic acid (3.37 g, 20.67 mmol) in sulfurous dichloride (30 ml.) was heated under refluxing for 4hrs. Sulfurous di- chloride was evaporated under reduced pressure to give the crude acid chloride.The crude material was dissolved in dichloromethane (20 ml.) and the solution was added dropwise to a solution of pyridin-3-amine (2.33 g, 24.81 mmol) and triethylamine (0.4 ml_, 4.134 mmol) in dichloromethane (20 ml_). The mixture was stirred overnight. The crude product was purified by prep-HPLC to give com- pound of example 7 as a yellow solid (4 g, yield 81 %).1H NMR (400 MHz, DMSO): δ 7.47-7.50 (m, 1 H), 8.22-8.23 (m, 1 H), 8.25-8.28 (m, 1 H), 8.38-8.40 (m, 1 H), 8.96 (s, 1 H), 9.00-9.02 (m, 1 H), 9.03-9.04 (m, 1 H), 9.70 (s, 1 H), 10.05 (s, 1 H).
	With thionyl chloride for 7h; Reflux;	24.a A suspension of pyrazolo[1 ,5-a]pyrazine-3-carboxylic acid (Preparation 23b, 6.70 g, 41.1 mmol) in thionyl chloride (50 ml_) was heated to reflux for 7 hours. After cooling, the reaction mixture was concentrated in vacuo and the residue was azeotroped with toluene (2 x 30 ml_). The resultant solid was suspended in 25% aqueous ammonium hydroxide solution (80 ml_) and the mixture was stirred for 16 hours at ambient temperature. The mixture was concentrated to dryness to give the crude title compound (10.0 g, >100%) as a beige solid which was used in the next synthetic step without further purification.LRMS (m/z): 163 (M+1)1H NMR δ (300 MHz, DMSO-cfe): 8.1 (d, 1 H), 8.7 (s, 1 H), 8.9 (d, 1 H), 9.6 (s,1 H).

	With thionyl chloride for 7h; Reflux;	90.c c) Pyrazolo[1,5-a]pyrazine-3-carboxamide: A suspension of pyrazolo[1,5-a]pyrazine-3-carboxylic acid (Preparation 90b, 6.70 g, 41.1 mmol) in thionyl chloride (50 mL) was stirred and heated to reflux. After 7 hours, the mixture was concentrated in vacuo and the residue was azeotroped with toluene (2 x 30 mL). The resultant solid was suspended in 25% aqueous ammonium hydroxide solution (80 mL) and the mixture was stirred for 16 hours at ambient temperature. The mixture was concentrated to dryness to give the crude title compound (10.0 g, >100%) as a beige solid which was used without further purification. LRMS (m/z): 163 (M+1)+.1H NMR (300 MHz, DMSO-d6) δ ppm 8.06 (d, 1H), 8.68 (s, 1H), 8.86 (d, 1H), 9.55 (s, 1H).
	With thionyl chloride for 7h; Reflux;	90.c c) Pyrazolo[1,5-a]pyrazine-3-carboxamide: A suspension of pyrazolo[1,5-a]pyrazine-3-carboxylic acid (Preparation 90b, 6.70 g, 41.1 mmol) in thionyl chloride (50 mL) was stirred and heated to reflux. After 7 hours, the mixture was concentrated in vacuo and the residue was azeotroped with toluene (2 x 30 mL). The resultant solid was suspended in 25% aqueous ammonium hydroxide solution (80 mL) and the mixture was stirred for 16 hours at ambient temperature. The mixture was concentrated to dryness to give the crude title compound (10.0 g, >100%) as a beige solid which was used without further purification. LRMS (m/z): 163 (M+1)+.1H NMR (300 MHz, DMSO-d6) δ ppm 8.06 (d, 1H), 8.68 (s, 1H), 8.86 (d, 1H), 9.55 (s, 1H).

Reference： [1]Qiao, Lixin; Choi, Sungwoon; Case, April; Gainer, Thomas G.; Seyb, Kathleen; Glicksman, Marcie A.; Lo, Donald C.; Stein, Ross L.; Cuny, Gregory D. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 21, p. 6122 - 6126]
[2]Current Patent Assignee: BASF SE - WO2010/34738, 2010, A2 Location in patent: Page/Page column 90
[3]Current Patent Assignee: ALMIRALL SA - WO2011/101161, 2011, A1 Location in patent: Page/Page column 100
[4]Current Patent Assignee: ALMIRALL SA - EP2397482, 2011, A1 Location in patent: Page/Page column 98
[5]Current Patent Assignee: ALMIRALL SA - WO2011/157397, 2011, A1 Location in patent: Page/Page column 162-163

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[ 53902-64-0 ]
[ 53902-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; water; lithium hydroxide at 70℃;

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[ 53975-16-9 ]
[ 623-47-2 ]
[ 53902-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl-formamide at 20℃;	A.2 A solution of N-aminopyrazine salt 1 (20 g, 20.83 mmol), ethyl propiolate (30.6 g,312.5 mmol) and K2CO3 (7.2g, 52.1 mmol) in dimethylformamide (200 mL) was stirred over night at room temperature. The solvent was evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate and the aqueous phase was extracted with ethyl acetate. The combined organic layers were concentrated. The residue was purified by column chromatography(petrol ether → petrol ether : ethyl acetate = 20) to yield a mixture of isomers of the bicyclic esters (3 g, yield 7.5 %) as a red solid. Saponification was then carried out using standard methods to give pyrazolo[1 ,5-a]pyrazine-3-carboxylic acid.

Reference： [1]Current Patent Assignee: BASF SE - WO2010/34738, 2010, A2 Location in patent: Page/Page column 89

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[ 53902-76-4 ]
[ 53902-93-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-Bromosuccinimide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 6h;	97.a PREPARATION 97 3-(Tributylstannyl)pyrazolo[1,5-a]pyrazine [Show Image]a) 3-Bromopyrazolo[1,5-a]pyrazine Sodium hydrogen carbonate (6.06 g, 72.1 mmol) and N-bromosuccinimide (4.28 g, 24.0 mmol) were added sequentially to a suspension of pyrazolo[1,5-a]pyrazine-3-carboxylic acid (Preparation 90b, 3.92 g, 24.0 mmol) in N,N'-dimethylformamide (67 mL) and the mixture was stirred at room temperature. After 6 hours, the mixture was partitioned between ethyl acetate and water and the aqueous phase was extracted with further ethyl acetate. The combined organic extract was dried (MgSO4) and evaporated and the residue was purified by flash chromatography (4:1 hexanes/ethyl acetate) to give the title compound (3.60 g, 76%) as a cream coloured solid. LRMS (m/z): 198/200 (M+1)+.H NMR (250 MHz, DMSO-d6) δ ppm 8.00 (d, 1H), 8.35 (s, 1H), 8.83 (dd, 1H), 9.11 (d, 1H).
76%	With N-Bromosuccinimide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 6h;	97.a PREPARATION 97 3-(Tributylstannyl)pyrazolo[1,5-a]pyrazine a) 3-Bromopyrazolo[1,5-a]pyrazine Sodium hydrogen carbonate (6.06 g, 72.1 mmol) and N-bromosuccinimide (4.28 g, 24.0 mmol) were added sequentially to a suspension of pyrazolo[1,5-a]pyrazine-3-carboxylic acid (Preparation 90b, 3.92 g, 24.0 mmol) in N,N'-dimethylformamide (67 mL) and the mixture was stirred at room temperature. After 6 hours, the mixture was partitioned between ethyl acetate and water and the aqueous phase was extracted with further ethyl acetate. The combined organic extract was dried (MgSO4) and evaporated and the residue was purified by flash chromatography (4:1 hexanes/ethyl acetate) to give the title compound (3.60 g, 76%) as a cream coloured solid. LRMS (m/z): 198/200 (M+1)+.H NMR (250 MHz, DMSO-d6) δ ppm 8.00 (d, 1H), 8.35 (s, 1H), 8.83 (dd, 1H), 9.11 (d, 1H).

Reference： [1]Current Patent Assignee: ALMIRALL SA - EP2397482, 2011, A1 Location in patent: Page/Page column 103-104
[2]Current Patent Assignee: ALMIRALL SA - WO2011/157397, 2011, A1 Location in patent: Page/Page column 169-170

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[ 1331756-52-5 ]