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[ CAS No. 1113-59-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 1113-59-3
Chemical Structure| 1113-59-3
Structure of 1113-59-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1113-59-3 ]

CAS No. :1113-59-3 MDL No. :
Formula : C3H3BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :PRRZDZJYSJLDBS-UHFFFAOYSA-N
M.W : 166.96 Pubchem ID :70684
Synonyms :
Bromopyruvic acid;Hexokinase II Inhibitor II, 3-BP;NSC 62343;NSC 11731;β-Bromopyruvic acid;3-BP;Hexokinase II Inhibitor II;3-Bromopyruvate

Calculated chemistry of [ 1113-59-3 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 26.38
TPSA : 54.37 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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.26
Log Po/w (XLOGP3) : 0.46
Log Po/w (WLOGP) : 0.04
Log Po/w (MLOGP) : -0.29
Log Po/w (SILICOS-IT) : 0.27
Consensus Log Po/w : 0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.03
Solubility : 15.5 mg/ml ; 0.0927 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 11.3 mg/ml ; 0.0676 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.45
Solubility : 59.0 mg/ml ; 0.353 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 1113-59-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1113-59-3 ]

* 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 [ 1113-59-3 ]
  • Downstream synthetic route of [ 1113-59-3 ]

[ 1113-59-3 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 1113-59-3 ]
  • [ 77287-34-4 ]
  • [ 3973-08-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 511 - 522
  • 2
  • [ 115-08-2 ]
  • [ 1113-59-3 ]
  • [ 3973-08-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 8, p. 2035 - 2044
  • 3
  • [ 1113-59-3 ]
  • [ 87-48-9 ]
  • [ 552330-94-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 2000 - 2007
[2] Patent: WO2011/87837, 2011, A2, . Location in patent: Page/Page column 30-31
[3] Patent: WO2012/87372, 2012, A1, . Location in patent: Page/Page column 30-31
  • 4
  • [ 1113-59-3 ]
  • [ 17356-08-0 ]
  • [ 5398-36-7 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 268
  • 5
  • [ 1113-59-3 ]
  • [ 95-54-5 ]
  • [ 62235-61-4 ]
Reference: [1] Patent: US4181724, 1980, A,
  • 6
  • [ 96-50-4 ]
  • [ 1113-59-3 ]
  • [ 53572-98-8 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 3, p. 412 - 415
  • 7
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 19, p. 3765 - 3766
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 511 - 522
[3] Helvetica Chimica Acta, 1946, vol. 29, p. 415,431
[4] Journal of Biological Chemistry, 1946, vol. 164, p. 437
[5] Journal of the Chemical Society, 1923, vol. 123, p. 2208
[6] Synthesis, 2006, # 15, p. 2563 - 2567
  • 8
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
Reference: [1] Patent: US4457936, 1984, A,
  • 9
  • [ 113-24-6 ]
  • [ 1113-59-3 ]
Reference: [1] International Journal of Chemical Kinetics, 2000, vol. 32, # 7, p. 408 - 418
  • 10
  • [ 14214-10-9 ]
  • [ 1113-59-3 ]
  • [ 70-23-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 467,472
  • 11
  • [ 123-54-6 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
  • [ 64-19-7 ]
  • [ 127-17-3 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 1, p. 1 - 6
  • 12
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1236 Anm. 1
[2] Bulletin de la Societe Chimique de France, 1874, vol. <2> 21, p. 391,393
[3] Chemische Berichte, 1868, vol. 1, p. 265[4] Justus Liebigs Annalen der Chemie, 1869, vol. 152, p. 264
  • 13
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
Reference: [1] International Journal of Chemical Kinetics, 2000, vol. 32, # 7, p. 408 - 418
  • 14
  • [ 123-54-6 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
  • [ 64-19-7 ]
  • [ 127-17-3 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 1, p. 1 - 6
  • 15
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1236 Anm. 1
[2] Bulletin de la Societe Chimique de France, 1874, vol. <2> 21, p. 391,393
[3] Chemische Berichte, 1868, vol. 1, p. 265[4] Justus Liebigs Annalen der Chemie, 1869, vol. 152, p. 264
  • 16
  • [ 67-56-1 ]
  • [ 1113-59-3 ]
  • [ 7425-63-0 ]
Reference: [1] Heterocycles, 2002, vol. 58, p. 471 - 504
[2] Patent: WO2006/20403, 2006, A2, . Location in patent: Page/Page column 58
  • 17
  • [ 64-17-5 ]
  • [ 1113-59-3 ]
  • [ 70-23-5 ]
Reference: [1] Patent: WO2006/20403, 2006, A2, . Location in patent: Page/Page column 59-60
  • 18
  • [ 14214-10-9 ]
  • [ 1113-59-3 ]
  • [ 70-23-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 467,472
  • 19
  • [ 1113-59-3 ]
  • [ 16982-21-1 ]
  • [ 911466-96-1 ]
YieldReaction ConditionsOperation in experiment
73% at 50℃; for 1.2 h; EXAMPLE 32Preparation of Intermediate Compound 32AA mixture of 3-bromopyruvic acid (16.37 g, 98.05 mmol) in anhydrous dioxane (90 ml_) was treated with ethyl thioamidooxalate (13.08 g, 98.22 mmol) for 1.2 h at 50 0C, and was then concentrated at 50 0C to yield a dry yellow solid. The crude product was dissolved in saturated sodium bicarbonate (150 mL) and water (150 mL). This solution was extracted with ethyl acetate (6 x 400 mL). The aqueous EPO <DP n="136"/>layer was then acidified to pH 2 with concentrated aqueous HCI (21 ml_), resulting in the formation of a heavy precipitate. This suspension was extracted with ethyl acetate (5 x 500 ml_). These extracts were pooled, dried with sodium sulfate, filtered, concentrated, and dried for about 15 hours under vacuum to yield compound 32A as a red-brown solid (14.36 g, 73percent yield) which was used without further purification.
62.8% at 60℃; for 16 h; 3-Bromo-2-oxopropanoic acid and ethyl amino(thioxo)acetate in THF (100 ml) were stirred at 60°C for 16 h. The reaction mixture was reduced in vacuo to give an orange solid. The solid was triturated with E0, filtered and dried in vacuo to give the titled compound (4.54 g, 62.8percent) as a colourless solid. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 13.40 (s, 1 H), 8.77 (s, 1 H), 4.40 (q, J = 7.1 Hz, 2H), 1 .35 (t, J = 7.1 Hz, 3H) HPLCMS (ESI+): [m/z]: 201.90 [M+H]+
Reference: [1] Patent: WO2008/54702, 2008, A1, . Location in patent: Page/Page column 134-135
[2] Patent: WO2017/68089, 2017, A2, . Location in patent: Page/Page column 258
[3] Patent: WO2009/58730, 2009, A1, . Location in patent: Page/Page column 54
[4] Patent: US2017/313691, 2017, A1, . Location in patent: Paragraph 0483-0485
  • 20
  • [ 5049-61-6 ]
  • [ 64-17-5 ]
  • [ 1113-59-3 ]
  • [ 1286754-14-0 ]
YieldReaction ConditionsOperation in experiment
28.9%
Stage #1: at 20 - 30℃; for 4 h;
Stage #2: for 4 h; Reflux
Step 1
ethyl imidazo[1,2-c]pyrazine-3-carboxylate
Pyrazin-2-amine 4a (1 g, 10 mmol) was dissolved in 50 mL of ethylene glycol dimethyl ether, followed by addition of 50 mL of methanol and 3-bromo-2-oxo-propionate (2.30 g, 12 mmol).
After stirring for 4 hours at room temperature, the reaction mixture was cooled to 0° C. and stirred for 30 minutes until a solid precipitated.
The reaction mixture was filtered, and the filter cake was washed with ether (10 mL*3).
The solid was dissolved in 50 mL of anhydrous ethanol and the solution was refluxed for 4 hours.
The reaction mixture was concentrated under reduced pressure, added with 100 mL of dichloromethane, washed successively with saturated sodium carbonate solution (40 mL) and saturated sodium chloride solution (40 mL), dried over anhydrous sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure to obtain ethyl imidazo[1,2-a]pyrazine-3-carboxylate 14a (0.55 g, yield 28.9percent) as a brown solid.
MS m/z (ESI): 192.1 [M+1]
Reference: [1] Patent: US2013/131068, 2013, A1, . Location in patent: Paragraph 0176; 0177
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