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

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Chemical Structure| 54013-06-8
Chemical Structure| 54013-06-8
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Product Details of [ 54013-06-8 ]

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

Calculated chemistry of [ 54013-06-8 ]

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 Ų

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: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 [ 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   1~62

  • 2
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YieldReaction ConditionsOperation 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.
  • 3
  • [ 1355999-71-1 ]
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  • [ 1447364-35-3 ]
YieldReaction ConditionsOperation 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) +.
  • 4
  • [ 1355999-71-1 ]
  • [ 54013-06-8 ]
  • [ 1447364-26-2 ]
YieldReaction ConditionsOperation 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).
  • 5
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  • [ 1610667-21-4 ]
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  • [ 1610668-64-8 ]
  • 7
  • [ 54013-06-8 ]
  • 3-{4-[(2S)-2-amino-2-cyclohexylacetamido]phenyl}-N-(4-cyanophenyl)-N-methylimidazo[1,2-a]pyrazine-6-carboxamide trifluoroacetate [ No CAS ]
  • 8
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  • [ 1610669-73-2 ]
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  • [ 1610667-04-3 ]
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  • [ 1610670-25-1 ]
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  • [ 1610670-23-9 ]
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  • [ 1610670-55-7 ]
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  • [ 1610667-74-7 ]
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  • [ 1610671-25-4 ]
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  • [ 1607830-85-2 ]
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  • [ 1610667-28-1 ]
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  • [ 1610667-36-1 ]
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  • [ 1610666-98-2 ]
  • 39
  • [ 78-95-5 ]
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  • [ 1610666-95-9 ]
YieldReaction ConditionsOperation in experiment
28% With triethylamine; In ethanol; at 170℃; for 0.5h;Microwave irradiation; To a solution of ethyl 5- aminopyrazine-2-carboxylate (668 mg, 4 mmol) in EtOH (25 mL) was added 1 -chloropropan-2- one (0.32 mL, 4 mmol) and triethylamine (0.83 mL, 6 mmol) and the mixture was heated in microwave synthesizer at 170 C for 30 min. The reaction mixture was cooled to RT and PAT054787-WO-PCT solvent was removed. The residue was purified by flash chromatography (silica gel, EtOAc/ hexanes) to afford 230 mg (28%) of I as white solid. 1 H NMR (400 MHz, CDCI3) delta 9.03 (s, 1 H), 8.92 (d, J = 1 .3, 1 H), 7.59 (s, 1 H), 4.51 (q, J = 7.1 , 2H), 2.61 - 2.53 (m, 3H), 1 .47 (t, J - 7.1 , 3H). HRMS calcd for C10H12N3O2 [M + H] + 205.09; found 206.1.
  • 40
  • [ 107-20-0 ]
  • [ 54013-06-8 ]
  • [ 588720-67-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In ethanol; water; at 90℃; for 16.0h; Chloroacetaldehyde (9.5 mL of a 50 wt% solution in water) was added to a mixture of aminopyrazine (2.00 g, 12.0 mmol), sodium bicarbonate (2.00 g, 23.8 mmol) and absolute ethanol (100 mL). The reaction was heated to 90 C for 16 hours. After cooling to room temperature, the reaction was concentrated and purified by flash chromatography (silica, 0-10% methanol/chloroform) to give pure 1-1 as a tan colored solid. 1 H NMR (400 MHz, CDCI3) delta 9.18 (s, 1 H), 9.01 (d, J= 1.4, 1 H), 7.93 (d, J= 1 .1 , 1 H), 7.84 (s, 1 H), 4.51 (q, J= 7.1 , 3H), 1 .46 (t, J = 7.1 , 4H).
  • 41
  • [ 431-35-6 ]
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  • [ 1610666-96-0 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 180℃; for 1.0h;Microwave irradiation; A mixture of aminopyrazine, 3-bromo-1,1,1-trifluoropropan-2-one and ethanol was heated in a microwave synthesizer at 180 C for 60 minutes. After cooling to room temperature, the solvent is removed and the dark brown residue is purified by flash chlromatography (silica, 30-60% ethyl acetate/hexanes) to give I-3 as a tan colored solid. 1H NMR (400 MHz, CDCI3) delta 9.24 (s, 1H), 8.99 (d, J= 1.4, 1H), 8.10 (s, 1H), 4.51 (q, J= 7.1, 2H), 1.46 (t, J= 7.1, 3H).
  • 42
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  • [ 1610667-56-5 ]
  • 43
  • [ 54013-06-8 ]
  • C14H9BrN6O [ No CAS ]
  • 44
  • [ 54013-06-8 ]
  • C13H11BrN6O [ No CAS ]
  • 45
  • [ 54013-06-8 ]
  • C15H10BrN5OS [ No CAS ]
  • 46
  • [ 54013-06-8 ]
  • C15H12BrFN4O [ No CAS ]
  • 47
  • [ 54013-06-8 ]
  • C14H18BrN5O [ No CAS ]
  • 48
  • [ 54013-06-8 ]
  • [ 1610668-19-3 ]
  • 49
  • [ 54013-06-8 ]
  • C21H13F3N6O [ No CAS ]
  • 50
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  • C20H15F3N6O [ No CAS ]
  • 51
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  • C22H14F3N5OS [ No CAS ]
  • 52
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  • [ 1610669-30-1 ]
  • 53
  • [ 54013-06-8 ]
  • C21H22F3N5O [ No CAS ]
  • 54
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  • [ 1610667-52-1 ]
  • 55
  • [ 54013-06-8 ]
  • [ 1607830-25-0 ]
  • 56
  • [ 54013-06-8 ]
  • ethyl 5-amino-6-bromopyrazine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N-Bromosuccinimide; In acetonitrile; at 20℃; for 1.0h; Step 1: Ethyl 5-amino-6-bromopyrazine-2-carboxylate: To a solution of <strong>[54013-06-8]ethyl 5-aminopyrazine-2-carboxylate</strong> (880 mg, 5.26 mmol) in acetonitrile (20 mL) at RT was added NBS (984 mg, 5.53 mmol), the resultant solution was stirred at RT for 1 hour. The reaction mixture was diluted with EtOAc, washed with sat NaHCO3, brine and water, dried, filtered, and concentrated to afford the crude product, which was purified by ISCO 24 g silica gel column, 0 to 50% EtOAc in Heptane, 30 min). 1.01 g, 78% yield. LC-MS (m/z): 247.9 (MH+), 0.51 min.
  • 57
  • [ 54013-06-8 ]
  • ethyl 5-amino-6-(4-(tert-butoxycarbonyl)-3-fluorophenyl)pyrazine-2-carboxylate [ No CAS ]
  • 58
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  • 4-(3-amino-6-(ethoxycarbonyl)pyrazin-2-yl)-2-fluorobenzoic acid [ No CAS ]
  • 59
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  • (S)-5-amino-6-(4-((1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamoyl)-3-fluorophenyl)pyrazine-2-carboxylic acid [ No CAS ]
  • 60
  • [ 54013-06-8 ]
  • (S)-4-(3-amino-6-(morpholine-4-carbonyl)pyrazin-2-yl)-N-(1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)-2-fluorobenzamide [ No CAS ]
  • 61
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  • (S)-ethyl 5-amino-6-(4-((1-(3-bromo-5-fluorophenyl)-2-hydroxyethyl)carbamoyl)-3-fluorophenyl)pyrazine-2-carboxylate [ No CAS ]
  • 62
  • (6-bromo-3-methyl-2-phenylquinolin-4-yl)(1H-imidazol-1-yl)methanone [ No CAS ]
  • [ 54013-06-8 ]
  • 5-[(6-bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}pyrazine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 3 5-[(6-Bromo-3-methyl-2-phenylquinolin-4-yl)carbonyl]amino}pyrazine-2-carboxylic acid (0773) (0774) 100 mg (0.26 mmol) of the compound from example 2A and 43 mg (0.26 mmol) of 377 <strong>[54013-06-8]ethyl 5-aminopyrazine-2-carboxylate</strong> were dissolved in 2 ml of 49 DMF. 72 mg (0.64 mmol) of 153 potassium tert-butoxide were added in portions to the solution. The reaction mixture was stirred at RT overnight, and then 1.3 ml (1.3 mmol) of 1 M 196 sodium hydroxide solution were added. After stirring at 80 C. for 1 h and cooling to RT, the mixture was adjusted to pH 1-2 with 1 M hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic phase was removed and washed with saturated sodium chloride solution. After the organic phase had been dried over sodium sulfate and the solvent had been removed on a rotary evaporator, the residue was taken up in a little DMF and purified by means of preparative HPLC (method 6). After the solvent-water mixture had been removed, the residue was taken up in a little acetonitrile, water was added and then the mixture was lyophilized. Since solvent residues were still present, the lyophilizate was redissolved in 124 dichloromethane and 61 ethyl acetate, 43 water was added again and the mixture was lyophilized again. The resulting lyophilizate was redissolved once again in dichloromethane and 378 tert-butanol, water was added and the mixture was lyophilized again. The lyophilizate thus obtained was dried at 100 C. under high vacuum for a total 9 h. In this way, 39 mg (29% of theory, 90% purity) of the 379 title compound were obtained. (0775) 1H-NMR (600 MHz, DMSO-d6): delta [ppm]=13.54 (br. s, 1H), 12.03 (s, 1H), 9.71 (s, 1H), 9.01 (s, 1H), 8.10 (d, 1H), 8.04 (d, 1H), 7.93 (dd, 1H), 7.66-7.60 (m, 2H), 7.58-7.50 (m, 3H), 2.41 (s, 3H). (0776) LC/MS (Method 1, ESIpos): Rt=0.96 min, m/z=463/465 [M+H]+.
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