[ CAS No. 54013-06-8 ] {[proInfo.proName]}

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Quality Control of [ 54013-06-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54013-06-8 ]

SDS Specification

Alternatived Products of [ 54013-06-8 ]

Product Details of [ 54013-06-8 ]

CAS No. :	54013-06-8	MDL No. :	MFCD08437665
Formula :	C₇H₉N₃O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	BLPDHDYKCBRILY-UHFFFAOYSA-N
M.W :	167.17	Pubchem ID :	22271413
Synonyms :

Calculated chemistry of [ 54013-06-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.52
TPSA :	78.1 ?2

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) :	-7.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	-0.07
Log Po/w (WLOGP) :	0.24
Log Po/w (MLOGP) :	-0.68
Log Po/w (SILICOS-IT) :	0.32
Consensus Log Po/w :	0.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.0
Solubility :	16.6 mg/ml ; 0.099 mol/l
Class :	Very soluble
Log S (Ali) :	-1.12
Solubility :	12.7 mg/ml ; 0.0761 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.77
Solubility :	2.86 mg/ml ; 0.0171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.13

Safety of [ 54013-06-8 ]

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

Application In Synthesis of [ 54013-06-8 ]

* 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 [ 54013-06-8 ]

[ 54013-06-8 ] Synthesis Path-Downstream 1~14

2
[ 1380646-44-5 ]
[ 13924-94-2 ]
[ 54013-06-8 ]
[ 1380646-64-9 ]
[ 1380645-91-9 ]

Yield	Reaction Conditions	Operation in experiment
12%; 20%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 20℃;	Example 15 5-[3-(4-Fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester To a suspension of a mixture of <strong>[54013-06-8]5-amino-pyrazine-2-carboxylic acid ethyl ester</strong> and 5-amino-pyrazine-2-carboxylic acid methyl ester (approximately 2:1) in CH2Cl2 (40 mL) was added DIEA (1.04 mL, 6 mmol) and DMF (5 mL). To the resulting suspension was added 3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)propionic acid (prepared as described in example 14, 1.5 g, 4.7 mmol), DMAP (0.17 g, 1.4 mmol) and EDC.HCl (1.08 g, 5.6 mmol) followed by additional CH2Cl2 (10 mL) and DMF (6 mL). The resulting solution was stirred at room temperature overnight. The reaction mixture was poured onto 0.01% aqueous HCl and extracted 3 times into CH2Cl2. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (silica, 30%-50% ethyl acetate/hexanes stepwise gradient), followed by re-purification of the mixed fractions by chromatography (50% ethyl acetate/hexanes) afforded the front-running product, 5-[3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester (438 mg, 20%): m.p. 99-100 C., LC/MS-ESI observed [M+H]+ 472; and the back-running product, 5-[3-(4-fluoro-phenyl)-2-(4-methanesulfonylphenyl)propionylamino]-pyrazine-2-carboxylic acid methyl ester (260 mg, 12%): m.p. 106-107 C., LC/MS-ESI observed [M+H]+ 458.

Reference： [1]Patent: US2012/149718,2012,A1 .Location in patent: Page/Page column 33

3
[ 1355999-71-1 ]
[ 54013-06-8 ]
[ 1447364-35-3 ]

Yield	Reaction Conditions	Operation in experiment
69 mg	With N-ethyl-N,N-diisopropylamine; at 120℃;Molecular sieve;	Intermediate Example lnt-5: Ethyl 2-(4-{1-[(ferf-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenyl- imidazo[1,2-a]pyrazine-6-carboxylate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (213 mg, 0.38 mmol, 1.0 eq), ethyl 5-aminopyrazine-2- carboxylate (CAS-Nr. 54013-06-8, 70.5 mg, 0.42 mmol, 1.1 eq.) and diisopropylethylamine (0.055 ml_, 0.42 mmol, 1.1 eq) in 2.3 ml_ butyronitrile was added pre- dried 3A mol sieves. The mixture was heated overnight at 120. The reaction mixture was partitioned between DCM/water and was filtered through a phase separator. The remaining volatile organic components were removed by the use of a rotary evaporator. In parallel we conducted the same experiment in the absence of diisopropylethylamine following the same protocol. The crude materials of both experiments were combined and purified via MPLC (Biotage Isolera, 25 g Snap- cartridge; eluent: hexane/ethyl acetate (1/1) -> ethyl acetate) to deliver 69 mg (14%, yield based on combined amount of fert-butyl (1-{4-[bromo(phenyl)acetyl]- phenyl}cyclobutyl)carbamate) of the title compound. UPLC-MS (Method 1): RT = 1.43 min; m/z = 513 (M+H) +.

Reference： [1]Patent: WO2013/104610,2013,A1 .Location in patent: Page/Page column 53-54

4
[ 1355999-71-1 ]
[ 54013-06-8 ]
[ 1447364-26-2 ]

Yield	Reaction Conditions	Operation in experiment
38 mg	at 120℃; for 1.5h;	Example 5: Ethyl 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2- a razine-6-carboxylate To a mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (245 mg, 0.44 mmol, 1.0 eq) and ethyl 5-aminopyrazine-2- carboxylate (CAS-Nr. 54013-06-8, 81.1 mg, 0.49 mmol, 1.1 eq.) in 2.7 mL bu- tyronitrile was heated at 120 for 1.5h. A substan tial amount of the deprotected free amine was detected by UPLC analysis. For isolation, the volatile components were removed using a rotary evaporator and the resulting crude material was purified via MPLC [Biotage Isolera, 25 g Snap-cartridge; eluent: DCM -> DCM/ethanol (95/5)] to deliver 38 mg (21 %) of the title compound. UPLC-MS (Method 1): RT = 0.90 min; m/z = 414 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 1.26 (t, 3H), 1.60 (m, 1 H), 1.88-2.07 (m, 3H), 2.12 (s br, 2H), 2.26-2.37 (m, 2H), 4.30 (q, 2H), 7.39 (d, 2H), 7.57(d, 4H), 7.60-7.68 (m, 3H).

Reference： [1]Patent: WO2013/104610,2013,A1 .Location in patent: Page/Page column 59-60

5
[ 54013-06-8 ]
[ 1610667-21-4 ]