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[ CAS No. 5521-58-4 ] {[proInfo.proName]}

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Chemical Structure| 5521-58-4
Chemical Structure| 5521-58-4
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Product Details of [ 5521-58-4 ]

CAS No. :5521-58-4 MDL No. :MFCD08437664
Formula : C5H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZNQOALAKPLGUPH-UHFFFAOYSA-N
M.W : 109.13 Pubchem ID :313215
Synonyms :

Calculated chemistry of [ 5521-58-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.4
TPSA : 51.8 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) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.95
Log Po/w (XLOGP3) : -0.23
Log Po/w (WLOGP) : 0.38
Log Po/w (MLOGP) : -0.72
Log Po/w (SILICOS-IT) : 0.69
Consensus Log Po/w : 0.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.93
Solubility : 12.9 mg/ml ; 0.118 mol/l
Class : Very soluble
Log S (Ali) : -0.4
Solubility : 43.4 mg/ml ; 0.398 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.62
Solubility : 2.64 mg/ml ; 0.0242 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 5521-58-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5521-58-4 ]

* 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.

  • Upstream synthesis route of [ 5521-58-4 ]
  • Downstream synthetic route of [ 5521-58-4 ]

[ 5521-58-4 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
78% With hydrogen; sodium hydroxide In methanol at 20℃; Inert atmosphere To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added benzyl(5-methylpyrazin-2-yl)carbamate (1.0 eq), palladium on carbon catalyst E196 (3percent w/w palladium on dry basis)), sodium hydroxide (0.01 eq)- and methanol (5 vols) under a nitrogen pad.
The reaction was de-gassed by pressurising and releasing under nitrogen, then charged with hydrogen to atmospheric pressure and the reaction agitated at 20+-5° C. for at least 3 hours.
Activated charcoal (Norit SX Ultra) (5percent wt charge) was added to the flask, the mixture was agitated for at least 30 minutes at 20+-5° C., then filtered through a 0.45 micron filter.
The filter was rinsed with methanol (1 vol) then the mother liquors allowed to stir at 15° C. under an atmosphere of 6percent oxygen/94percent nitrogen for up to 24 hours (alternatively an atmosphere of 1percent oxygen/99percent nitrogen was used), then re-filtered through the 0.45 micron filter.
The mother liquors were vacuum distilled at 45° C. to a final volume of 1.5 vols.
Toluene (1.5 vols) was added and the mixture vacuum distilled at 45° C. to a final volume of 1.5 vols.
This process was repeated with further toluene (0.5 vols) then the resulting mixture was cooled to 5° C. and filtered.
The solid was washed with toluene (1 vol).
The solid was washed with toluene (1 vol).
After drying in the vacuum oven at 40° C. overnight, the desired product was obtained as a solid (corrected yield 65-78percent).
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 1, p. 77 - 81
[2] Patent: US2010/210841, 2010, A1, . Location in patent: Page/Page column 21
  • 2
  • [ 625114-66-1 ]
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YieldReaction ConditionsOperation in experiment
76% With hydrogen In ethanol at 25℃; for 1 h; [0386] A mixture of 5-methylpyrazine-2-carboxylic acid (2.76 g, 20 mmol) and oxalyl chloride (1.83 mL, 2.66 g, 21 mmol) in methylene chloride (40 mL) was treated with N,N-dimethylformamide (0.5 mL), and the mixture was stirred at 25° C. for 1 h. The mixture was filtered, and the filtrate was concentrated in vacuo to give an oily solid. The solid was dissolved in acetone (120 mL) at 0° C. and then sodium azide (1.03g, 20 mmol) in water (50 mL) was added dropwise. After the addition was complete, stirring was continued at 0° C. for 30 min. The mixture was then poured into ice cold water (100 mL) and extracted with methylene chloride (3.x.100 mL). The combined organic extracts were washed with water (1.x.100 mL), a mixture of a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution (1:1, 1.x.100 mL), and dried over anhydrous sodium sulfate. The mixture was filtered and concentrated in vacuo to give 5-methyl-pyrazine-2-carbonyl azide (1.46 g, 45percent) as a tan solid. The 5-methyl-pyrazine-2-carbonyl azide (500 mg, 3.07 mmol) was combined with benzyl alcohol (0.63 mL, 663 mg, 6.14 mmol) at 25° C. The mixture was then slowly heated on an oil bath to 90° C., upon which gas was violently evolved. The oil bath temperature was maintained until gas evolution ceased. The oil bath temperature was raised to 120° C. and stirring was continued for 10 min at that temperature. The mixture was cooled and triturated with diethyl ether/hexanes (1:4) to give (5-methylpyrazin-2-yl)-carbamic acid phenyl ester (438 mg, 58percent) as a yellow solid. The (5-methylpyrazin-2-yl)-carbamic acid phenyl ester (500 mg, 2.2 mmol) and 10percent palladium on carbon (212 mg) were mixed in ethanol (30 mL). The reaction vessel was flushed with hydrogen, and the mixture was stirred at 25° C. for 1 h under hydrogen (1 atm). The excess hydrogen was evacuated from the reaction vessel, and the mixture was filtered through a pad of celite. Concentration of the filtrate in vacuo gave 2-amino-5-methylpyrazine (183 mg, 76percent) as a tan solid which was used without further purification. [0387] A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid (prepared as in Example 60, 263 mg, 0.73 mmol) and triphenylphosphine (250 mg, 0.95 mmol) in methylene chloride (5.0 mL) cooled to 0° C. was treated with N-bromosuccinimide (167 mg, 0.95 mmol) in small portions. After the complete addition of N-bromosuccinimide, the reaction mixture was allowed to warm to 25° C. over 30 min. The bright orange reaction mixture was then treated with 2-amino-5-methylpyrazine (160 mg, 1.46 mmol) and 2,6-lutidine (0.36 mL, 2.92 mmol). The resulting reaction mixture was stirred at 25° C. for 4 h. The reaction mixture was then diluted with methylene chloride (25 mL) and was successively washed with a 10percent aqueous hydrochloric acid solution (1.x.20 mL), a saturated aqueous sodium bicarbonate solution (1.x.20 mL) and water (1.x.20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 65/35 hexanes/ethyl acetate to 3/7 hexanes/ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-methyl-pyrazin-2-yl)-3-(4-oxo-cyclohexyl)-propionamide (158 mg, 48percent) as a white foam: [α]23589=-41.52° (c=0.33, chloroform); EI-HRMS m/e calcd for C20H21Cl2N3O4S (M+H)+ 450.1249, found 450.1253.
Reference: [1] Patent: US2003/225283, 2003, A1, . Location in patent: Page 50
  • 3
  • [ 369638-68-6 ]
  • [ 5521-58-4 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 65 - 75℃;
Stage #2: With sodium hydroxide In water at 15 - 40℃;
To a flask fitted with overhead stirrer, condenser, thermometer and nitrogen line was added tert-butyl (5-methylpyrazin-2-yl)carbamate (1.0 eq), and water (6.85 vols).
The mixture was heated to 70° C. and trifluoroacetic acid (TFA) (1.2 eq) was added slowly drop-wise over 90-120 minutes.
Water (0.22 vols) was added to wash the TFA into the flask.
The reaction mixture was heated at 65-75° C. for at least 30 minutes, and then cooled to 15-25° C. Then 32percent w/w sodium hydroxide (1.30 eq) was added drop-wise over 30-60 minutes maintaining the reaction temperature between 15-40° C. Water (0.22 vols) was added to wash the sodium hydroxide into the flask. N-Propylacetate (7.0 vols) was added and the mixture agitated for 45 minutes at 20° C.
The layers were separated, the organic layer was retained and the aqueous layer was returned to the flask. N-Propylacetate (7.0 vols) was added and the mixture agitated for 45 minutes at 20° C.
The layers were separated, the organic layer was retained and the aqueous layer was returned to the flask.
This process was repeated twice.
The combined organic layers were filtered through a filter containing silica (20percent w/w) into a clean dry flask.
The mixture was heated to 40° C. and then vacuum distilled to a final volume of 1.0-1.33 vols.
Toluene (3.0 vols) was added, and the vacuum distillation continued at 40° C. to a final volume of 1.0-1.33 vols.
This process was repeated twice.
The resulting mixture was cooled to 5° C., and agitated for 1 hour at this temperature then filtered, washed with toluene (0.3 vols) at 0-5° C.
The batch is slurry washed with toluene (1.0 vol) at 0-5° C.
After drying at 45° C. overnight, the desired product was obtained as a solid (corrected yield typically 75percent).
1H NMR δ (400 MHz CDCl3): 7.92 (s, 1H), 7.87 (s, 1H), 4.6 (bs, 2H), 2.40 (s, 3H)
74%
Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 4 h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
A. 5-methylpyrazin-2-amine; To a solution tert-butyl 5-methylpyrazin-2-ylcarbamate (1.5 g, 7.17 mmol) in CH2CI2 (20 ml) was added TFA (2.6 mL, 35.86 mmol). The reaction mixture was stirred for 4 hours at room temperature after which, it was concentrated under reduced pressure. The reaction mixture was diluted with CH2CI2 and neutralized with sai.NaHCOs solution. The organic layer was separated and the aqueous layer was extracted with CH2CI2. The combined organic extracts were washed with brine, dried over MgS04, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (30percent to 50percent Ethyl acetate/Hexane) as a solvent to afford title compound (580 mg, 74percent yield). MS m/z : 110 [M+l] .
Reference: [1] Patent: US2010/210841, 2010, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2011/90738, 2011, A2, . Location in patent: Page/Page column 50
[3] Patent: US2003/69284, 2003, A1,
[4] Patent: US2010/113510, 2010, A1, . Location in patent: Page/Page column 46
[5] Patent: EP2781508, 2014, A1, . Location in patent: Paragraph 0154
[6] Patent: US2014/303186, 2014, A1, . Location in patent: Paragraph 0299
  • 4
  • [ 19994-56-0 ]
  • [ 5521-58-4 ]
Reference: [1] Patent: WO2006/105262, 2006, A1, . Location in patent: Page/Page column 65
  • 5
  • [ 74290-65-6 ]
  • [ 5521-58-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
  • 6
  • [ 96-26-4 ]
  • [ 69816-37-1 ]
  • [ 141-46-8 ]
  • [ 5521-58-4 ]
Reference: [1] Journal of the American Society for Mass Spectrometry, 2016, vol. 27, # 5, p. 897 - 907
  • 7
  • [ 109-60-4 ]
  • [ 76-05-1 ]
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Reference: [1] Patent: US2010/210621, 2010, A1,
  • 8
  • [ 59303-10-5 ]
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Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1580,1582
  • 9
  • [ 17280-41-0 ]
  • [ 6011-14-9 ]
  • [ 5521-58-4 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 51, p. 9287 - 9290
  • 10
  • [ 5521-57-3 ]
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Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 802,804
  • 11
  • [ 20721-17-9 ]
  • [ 5521-58-4 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1580,1582
  • 12
  • [ 5521-55-1 ]
  • [ 5521-58-4 ]
Reference: [1] Patent: WO2011/90738, 2011, A2,
[2] Patent: EP2781508, 2014, A1,
[3] Organic Process Research and Development, 2018, vol. 22, # 1, p. 77 - 81
  • 13
  • [ 5521-58-4 ]
  • [ 89464-87-9 ]
Reference: [1] Patent: WO2018/136265, 2018, A1,
  • 14
  • [ 5521-58-4 ]
  • [ 74290-65-6 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; bromine In dichloromethane at 20℃; To a solution of 5-methylpyrazin-2-amine (5.00g, 45.8 mmol) and pyridine (4.35g,55.0 mmol) in DCM (250 mL) was added bromine (8.80 g, 55.0 mmol). The mixture was stirredat rt overnight. To the reaction mixture was added water (150 mL), and the resulting mixture waspartitioned. The organic layer was washed with saturated brine (100 mL), dried over anhydroussodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound asa yellow solid (7.64 g, 88 percent).MS (ESI, pos. ion) m/z: 190.2 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 7.83 (s, lH), 4.93 (s, 2H), 2.41 (s, 3H).
69% With N-Bromosuccinimide In dichloromethane at 0 - 30℃; for 1 h; Inert atmosphere [00790] To a mixture of 5-methylpyrazin-2-amine (10 g, 92 mmol) in DCM (300 mL) was added BS (16 g, 91.63 mmol) in one portion at 0 °C under N2. The mixture was stirred at 30 °C for 1 hr. The resulting mixture was poured into saturated aq. Na2S03 (100 mL) and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 3-bromo-5-methyl-pyrazin-2-amine (12 g, 69percent yield,) as a light yellow solid. MR (400 MHz, CDCh-d) δ ppm 7.82 (s, 1H) 4.79 - 5.03 (m, 2 H) 2.39 (s, 3 H).
65% With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 12 h; Step 1.
3-Bromo-5-methylpyrazin-2-amine.
To a cooled, 0° C., solution of 5-methylpyrazin-2-amine (5.00 g, 0.05 mol) in DCM (230 mL) was added 1-bromopyrrolidine-2,5-dione (8.97 g, 0.05 mol) all at once.
The reaction mixture was allowed to warm to room temperature and stirred for 12 h.
The reaction was quenched with 1 N sodium thiosulfate (50 mL), the layers were separated and the organic phase was extracted with water (2*50 mL).
The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure.
Purification (FCC, SiO2, 0-50percent, EtOAc/hexanes) afforded the title compound as a yellow solid (8.61 g, 65percent).
[M+H]=188.9/190.11
56.4% With pyridine; bromine In chloroform for 0.5 h; To a suspension of 5-methylpyrazin-2-amine (1.09g, 10 mmol) in chloroform (100 mL) was added pyridine(0.85 ml., 10.5 mmol). The mixture was stirred in a foilwrappedflask fitted with an addition funnel, and a solution ofbromine (0.54 ml., 10.5 mmol) in chloroform (10 mL) wasadded dropwise over 10 min. The mixture was allowed toreact an additional 20 minutes after addition was completeand then poured into a separatory funnel containing 10 mLwater. The phases were separated and the organics washedagain with water, dried over sodium sulfate, filtered and concentratedin vacuo. The resulting red oil was purified by silicagel chromatography with 12-100percent EtOAc/hexanes. Themajor UV active peak was collected to give 3-bromo-5-methylpyrazin-2-amine (1.06 g, 5.64 mmol, 56.4percent yield) as a cream-colored solid.

Reference: [1] Patent: WO2018/108125, 2018, A1, . Location in patent: Paragraph 00511
[2] Patent: WO2018/136265, 2018, A1, . Location in patent: Paragraph 00790
[3] Patent: US2014/275531, 2014, A1, . Location in patent: Paragraph 0353
[4] Patent: JP5714745, 2015, B2, . Location in patent: Paragraph 0687; 0688
[5] Patent: US5866568, 1999, A,
[6] Patent: US5668137, 1997, A,
  • 15
  • [ 5521-58-4 ]
  • [ 74290-65-6 ]
  • [ 74290-68-9 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With hydrogen bromide; acetic acid In chloroform at 50℃; for 0.5 h; Darkness
Stage #2: With bromine In chloroform at 55℃; for 21 h;
Stage #3: With sodium carbonate In chloroform; water
A solution of HBr/CH3CO2H (360 g (260 mL), 1.50 mol, 33percent HBr in CH3CO2H) in anhydrous CHCl3 (300 mL) was added over 15 min to a solution of 5-methylpyrazin-2-amine 15 (42 g, 0.38 mmol) in CHCl3 (1 L). The reaction flask was wrapped in aluminum foil and heated to 50 °C for 30 min in the dark whereupon a solution of Br2 (68 g, 0.42 mmol) in CHCl3 (500 mL) was added dropwise over 3 h during which time the internal temperature of the reaction never exceeded 55 °C. After 18 h at 55 °C the solvent was evaporated under reduced pressure. The crude mixture was diluted with water (200 mL) and the pH was adjusted to pH=9 by the addition of solid Na2CO3. The suspension was filtered under vacuum and the filtrate was extracted with EtOAc (1 L.x.5). The combined organic extracts were concentrated under reduced pressure and purified by flash silica gel chromatography eluting with petroleum ether/EtOAc (5:1-->1:1) to give compound 6-bromo-5-methylpyrazin-2-amine 17a (36 g, 50percent) as a light orange solid; mp 154-157 °C; IR (KBr): 3315, 3188, 1744, 1638, 1575, 1482, 1375, 1308, 1051 cm-1; 1H NMR (400 MHz, CDCl3): δ=7.84 (s, 1H), 4.55 (br s, 2H), 2.52 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=152.2, 141.8, 138.4, 129.2, 22.2; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9816 and 189.9796. An analytical sample of 3-bromo-5-methylpyrazin-2-amine (17b) was also isolated for spectroscopic analysis; mp 56-57 °C. 1H NMR (400 MHz, CDCl3): δ=7.80 (s, 1H), 4.95 (br s, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=150.6, 142.8, 139.9, 125.2, 19.7; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9817 and 189.9796.
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
[2] Tetrahedron, 2011, vol. 67, # 47, p. 9063 - 9066
  • 16
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  • [ 74290-65-6 ]
  • [ 74290-68-9 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With hydrogen bromide; acetic acid In chloroform at 50℃; for 0.5 h; Darkness
Stage #2: With bromine In chloroform at 55℃; for 21 h;
Stage #3: With sodium carbonate In chloroform; water
A solution of HBr/CH3CO2H (360 g (260 mL), 1.50 mol, 33percent HBr in CH3CO2H) in anhydrous CHCl3 (300 mL) was added over 15 min to a solution of 5-methylpyrazin-2-amine 15 (42 g, 0.38 mmol) in CHCl3 (1 L). The reaction flask was wrapped in aluminum foil and heated to 50 °C for 30 min in the dark whereupon a solution of Br2 (68 g, 0.42 mmol) in CHCl3 (500 mL) was added dropwise over 3 h during which time the internal temperature of the reaction never exceeded 55 °C. After 18 h at 55 °C the solvent was evaporated under reduced pressure. The crude mixture was diluted with water (200 mL) and the pH was adjusted to pH=9 by the addition of solid Na2CO3. The suspension was filtered under vacuum and the filtrate was extracted with EtOAc (1 L.x.5). The combined organic extracts were concentrated under reduced pressure and purified by flash silica gel chromatography eluting with petroleum ether/EtOAc (5:1-->1:1) to give compound 6-bromo-5-methylpyrazin-2-amine 17a (36 g, 50percent) as a light orange solid; mp 154-157 °C; IR (KBr): 3315, 3188, 1744, 1638, 1575, 1482, 1375, 1308, 1051 cm-1; 1H NMR (400 MHz, CDCl3): δ=7.84 (s, 1H), 4.55 (br s, 2H), 2.52 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=152.2, 141.8, 138.4, 129.2, 22.2; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9816 and 189.9796. An analytical sample of 3-bromo-5-methylpyrazin-2-amine (17b) was also isolated for spectroscopic analysis; mp 56-57 °C. 1H NMR (400 MHz, CDCl3): δ=7.80 (s, 1H), 4.95 (br s, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=150.6, 142.8, 139.9, 125.2, 19.7; HRMS-ESI: calcd for C5H7BrN3 (M+H)+: 187.9823 and 189.9803; found: 187.9817 and 189.9796.
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147
[2] Tetrahedron, 2011, vol. 67, # 47, p. 9063 - 9066
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