[ CAS No. 710322-57-9 ] {[proInfo.proName]}

Name: 710322-57-9|Methyl 5-formylpyrazine-2-carboxylate|98%
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SKU: A318228
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Quality Control of [ 710322-57-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 710322-57-9 ]

CAS No. :	710322-57-9	MDL No. :	MFCD12755910
Formula :	C₇H₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNAAFIKYVYERNG-UHFFFAOYSA-N
M.W :	166.13	Pubchem ID :	44515461
Synonyms :

Calculated chemistry of [ 710322-57-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.7
TPSA :	69.15 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) :	-7.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.66
Log Po/w (XLOGP3) :	-0.7
Log Po/w (WLOGP) :	0.08
Log Po/w (MLOGP) :	-1.44
Log Po/w (SILICOS-IT) :	0.86
Consensus Log Po/w :	-0.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.6
Solubility :	41.6 mg/ml ; 0.251 mol/l
Class :	Very soluble
Log S (Ali) :	-0.28
Solubility :	87.8 mg/ml ; 0.528 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.67
Solubility :	3.55 mg/ml ; 0.0214 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.87

Safety of [ 710322-57-9 ]

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 [ 710322-57-9 ]

* 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 [ 710322-57-9 ]
Downstream synthetic route of [ 710322-57-9 ]

[ 710322-57-9 ] Synthesis Path-Upstream 1~3

1
[ 710322-24-0 ]
[ 710322-57-9 ]

Reference： [1] Patent: WO2004/52869, 2004, A1, . Location in patent: Page 140

2
[ 64-17-5 ]
[ 866327-72-2 ]
[ 710322-57-9 ]

Reference： [1] Patent: US2005/222151, 2005, A1, . Location in patent: Page/Page column 19-20

3
[ 41110-33-2 ]
[ 710322-57-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 11, p. 4413 - 4425

[ 710322-57-9 ] Synthesis Path-Downstream 1~21

1
[ 710322-57-9 ]
[ 107-21-1 ]
[ 710322-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	With p-toluenesulfonic acid monohydrate; In benzene; for 17h;Heating / reflux;	[000243] A mixture of <strong>[710322-57-9]5-formyl-pyrazine-2-carboxylic acid methyl ester</strong> (325 mg, 1.56 mmol), ethylene glycol (100 pL, 1.79 MMOL), and p-toluenesulfonic acid monohydrate (30 mg, 0.157 mmol) in benzene (10 mL) was heated under reflux with a Dean-Stark condenser for 17 h. The mixture was cooled and diluted with benzene (25 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (25 ML) and a saturated aqueous sodium chloride solution (25 mL). Each aqueous wash was back-extracted with a small portion of benzene. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to afford 5- [L, 3dioxolan-2-yl-pyrazine-2-carboxylic acid methyl ester as an orange-red oil (250 mg).

Reference： [1]Patent: WO2004/52869,2004,A1 .Location in patent: Page 140 - 141

2
[ 710322-24-0 ]
[ 710322-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; In tetrahydrofuran; water; at 25℃; for 0.5h;	[000242] A solution of the 5- (2-dimethylamino-vinyl)-pyrazine-2-carboxylic acid methyl ester (415 mg, 2.0 mmol) in tetrahydrofuran and water (10 mL, 1: 1) was treated with powdered sodium periodate (1.3 g, 6.07 mmol). The mixture was stirred at 25C for 30 min, at which time, thin layer chromatography suggested complete conversion to a product less polar than starting material. The reaction mixture was concentrated ILL vacuo nearly to dryness, and the residue was partitioned with ethyl acetate (50 mL) and a saturated aqueous sodium bicarbonate solution (25 mL). The aqueous phase was extracted with ethyl acetate (2 x 50 mL). Each of the organic extracts was washed with a saturated aqueous sodium chloride solution (25 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude aldehyde, 5-formyl-pyrazine-2-carboxylic acid methyl ester (180 mg), as an orange oil which was used without further characterization or purification.

Reference： [1]Patent: WO2004/52869,2004,A1 .Location in patent: Page 140

3
[ 110-89-4 ]
[ 710322-57-9 ]
[ 866327-73-3 ]

Yield	Reaction Conditions	Operation in experiment
23%		A mixture of <strong>[710322-57-9]5-formyl-pyrazine-2-carboxylic acid methyl ester</strong> (0.400 g, 2.40 mmol), piperidine (0.204 g, 2.40 mmol), and NaB(OAc)3H (1.40 g, 3.60 mmol) in DCM (10 mL) was stirred for 18 h at rt. The reaction was quenched by the addition of 10% aq. NaOH (10 mL) and the mixture was stirred for 30 min. The mixture was extracted with DCM (3*20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to yield the title compound (0.130 g, 23%).

Reference： [1]Patent: US2005/222151,2005,A1 .Location in patent: Page/Page column 20
[2]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4413 - 4425

4
[ 64-17-5 ]
[ 866327-72-2 ]
[ 710322-57-9 ]

Yield	Reaction Conditions	Operation in experiment
	With silver nitrate; In tetrahydrofuran; water; at 80℃; for 1.25h;	A solution of 5-dibromomethyl-pyrazine-2-carboxylic acid methyl ester (1.00 g, 3.23 mmol) in a mixture of ethanol (20 mL) and THF (10 mL) was heated to 80 C. A solution of silver nitrate (2.20 g, 12.9 mmol) in H2O (4 mL) was added. The reaction mixture was heated at 80 C. for 1.25 h and was filtered while hot. The filtrate was concentrated to yield the title compound (1.36 g). This material was carried to the next step without purification.

Reference： [1]Patent: US2005/222151,2005,A1 .Location in patent: Page/Page column 19-20

5
[ 110-91-8 ]
[ 710322-57-9 ]
5-(morpholin-4-yl)methylpyrazine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4413 - 4425

6
[ 41110-33-2 ]
[ 710322-57-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4413 - 4425

7
[ 710322-57-9 ]
[ 1262803-64-4 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl 5-(hvdroxymethyl)pyrazine-2-carboxylate 29-(l)To a solution of <strong>[710322-57-9]methyl 5-formylpyrazine-2-carboxylate</strong> (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (I N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3 x 40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 3H), 4.98 (br. s., 2H), 8.80 (s, IH), 9.27 (s, IH)
		To a solution of <strong>[710322-57-9]methyl 5-formylpyrazine-2-carboxylate</strong> (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (1 N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3×40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 3H), 4.98 (br. s., 2H), 8.80 (s, 1H), 9.27 (s, 1H)
		To a solution of <strong>[710322-57-9]methyl 5-formylpyrazine-2-carboxylate</strong> (2.47 g) in THF (20 mL) was added sodium borohydride (170 mg) portionwise over 10 mins. After stirring for 1 h, methanol (10 mL) was added. The reaction mixture was stirred for a further 20 mins, and then HCl (1 N, aq., 20 mL) and brine (20 mL) were added. The mixture was extracted with EtOAc (3×40 mL) and the combined organic portions dried over MgSO4 and evaporated to afford the title compound (1.31 g). 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 3H), 4.98 (br. s., 2H), 8.80 (s, 1H), 9.27 (s, 1H)

Reference： [1]Patent: WO2011/9898,2011,A1 .Location in patent: Page/Page column 100-101
[2]Patent: US2012/190672,2012,A1 .Location in patent: Page/Page column 31
[3]Patent: WO2012/98213,2012,A1 .Location in patent: Page/Page column 62-63

8
[ 710322-57-9 ]
[ 1262803-65-5 ]

Reference： [1]Patent: WO2011/9898,2011,A1
[2]Patent: US2012/190672,2012,A1

9
[ 710322-57-9 ]
[ 1262803-66-6 ]

Reference： [1]Patent: WO2011/9898,2011,A1
[2]Patent: US2012/190672,2012,A1

10
[ 710322-57-9 ]
[ 1388149-44-7 ]

Reference： [1]Patent: US2012/190672,2012,A1
[2]Patent: US2012/190672,2012,A1

11
[ 710322-57-9 ]
[ 1388149-34-5 ]

Reference： [1]Patent: US2012/190672,2012,A1

12
[ 710322-57-9 ]
[ 1388149-35-6 ]

Reference： [1]Patent: US2012/190672,2012,A1

13
[ 710322-57-9 ]
[ 1388149-45-8 ]

Reference： [1]Patent: US2012/190672,2012,A1

14
[ 710322-57-9 ]
(S)-N-[(1E)-1-(2-hydroxy-4-methoxyphenyl)ethylidene]-2-methylpropane-2-sulfinamide [ No CAS ]
methyl 5-[(1S,3E)-1-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3-[(S)-2-methylpropane-2-sulfinyl]imino}propyl]pyrazine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 144A methyl 5-[(1S,3E)-1-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3-[(S)-2-methylpropane-2-sulfinyl]imino}propyl]pyrazine-2-carboxylate A solution of diisopropylamine (163 muL, 1.143 mmol) in tetrahydrofuran (2 mL) under N2 at -20 C. was treated with 2.5 M n-butyllithium in hexanes (437 muL, 1.091 mmol) and stirred for 15 minutes. In a separate flask, a solution of the product from Example 89A (140 mg, 0.520 mmol) in tetrahydrofuran (2 mL) under N2 at -20 C. was treated over 1 minute with the lithium diisopropyl amine solution. The mixture was stirred at -20 C. for 1 hour, cooled to -78 C., and treated with a solution of <strong>[710322-57-9]methyl 5-formylpyrazine-2-carboxylate</strong> (CAS No.710322-57-9) (86 mg, 0.520 mmol) in tetrahydrofuran (1.5 mL). The reaction mixture was warmed to 0 C., cooled to -30 C., treated with a solution of 10% acetic acid in tetrahydrofuran (about 1.5 mL) and allowed to warm to room temperature. The mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The ethyl acetate layer was washed with brine, dried (MgSO4), filtered, and concentrated. The crude material on chromatographed on silica gel and eluted with a gradient of 25-100% ethyl acetate in heptanes. The collected fractions were concentrated and chromatographed on silica gel and eluting with a gradient of 50% ethyl acetate in CH2Cl2 to provide the title compound. 1H NMR (501 MHz, CDCl3) delta 13.04 (s, 1H), 9.26 (d, J=1.4 Hz, 1H), 8.82-8.81 (m, 1H), 7.14 (d, J=9.2 Hz, 1H), 6.38 (d, J=2.6 Hz, 1H), 6.19 (dd, J=9.1, 2.6 Hz, 1H), 5.43 (q, J=5.0 Hz, 1H), 5.06 (d, J=4.6 Hz, 1H), 4.04 (s, 3H), 3.91 (dd, J=13.6, 6.4 Hz, 1H), 3.85 (dd, J=13.7, 5.2 Hz, 1H), 3.79 (s, 3H), 1.40 (s, 9H). LC/MS (ESI+) m/z 436 (M+H)+.

Reference： [1]Patent: US2017/15675,2017,A1 .Location in patent: Paragraph 1290

15
[ 710322-57-9 ]
sodium 5-(dimethoxymethyl)pyrazinecarboxylate [ No CAS ]