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[ CAS No. 188011-69-0 ] {[proInfo.proName]}

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Chemical Structure| 188011-69-0
Chemical Structure| 188011-69-0
Structure of 188011-69-0 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 188011-69-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 188011-69-0 ]

SDS Specification
Alternatived Products of [ 188011-69-0 ]

Product Details of [ 188011-69-0 ]

CAS No. :188011-69-0 MDL No. :MFCD00116442
Formula : C9H9BrN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XFYYQDHEDOXWGA-UHFFFAOYSA-N
M.W : 273.08 Pubchem ID :647833
Synonyms :
Abrasin
Chemical Name :4-((5-Bromopyridin-2-yl)amino)-4-oxobutanoic acid

Calculated chemistry of [ 188011-69-0 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.64
TPSA : 79.29 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) : -7.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.86
Log Po/w (XLOGP3) : 0.48
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 0.34
Log Po/w (SILICOS-IT) : 1.21
Consensus Log Po/w : 0.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 4.31 mg/ml ; 0.0158 mol/l
Class : Very soluble
Log S (Ali) : -1.71
Solubility : 5.27 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.237 mg/ml ; 0.000869 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.9

Safety of [ 188011-69-0 ]

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

Application In Synthesis of [ 188011-69-0 ]

* 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 [ 188011-69-0 ]

[ 188011-69-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 108-30-5 ]
  • [ 1072-97-5 ]
  • [ 188011-69-0 ]
YieldReaction ConditionsOperation in experiment
84% In acetone for 4h; Heating;
Reference： [1]Burdulene; Stumbryavichyute; Talaikite; Vladyko; Boreko; Korobchenko [Pharmaceutical Chemistry Journal, 1996, vol. 30, # 11, p. 680 - 682]
YieldReaction ConditionsOperation in experiment
65%
  • 3
  • [ 461-18-7 ]
  • Bikinin [ No CAS ]
  • [ 1443415-55-1 ]
YieldReaction ConditionsOperation in experiment
80% With thionyl chloride at 70℃; for 2.08333h; I Example I: Synthesis of 4,4,4-trifluorobutyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate Al Thionyl chloride (Commercialy available, 3 equiv., 2 mmol) was added drop wise to 4, 4, 4- trifluorobutan-l-ol (2 mL). When the exothermic addition was finish, the reaction was stirred for 5 minutes and 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoic acid (Commercialy available, 0.2 g, 0.7 mmol) was added. The solution was stirred at 70°C for 2 hours. The reaction was cooled and quenched by addition of water. The aqeuous layer was extracted with ethyl acetate and washed with a saturated solution of sodium hydrogenocarbonate. After separation, the organic phase was dried and concentrated under vacuum to give 4,4,4- trifluorobutyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate Al (0.22 g, 80%). Mp= 118- 119 °C, 1H MR (400 MHz, CDC13) δ 8.32 (m, 2H), 8.12 (d, 1H), 7.78(dd, 1H), 4.20 (m, 2H), 2.74 (m, 4H), 2.20 (m, 2H), 1.92 (m, 2H) ppm.
80% Stage #1: 4,4,4-trifluorobutanol With thionyl chloride for 0.0833333h; Stage #2: Bikinin at 70℃; for 2h; I Synthesis of 4,4,4-trifluorobutyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate A1 Example I Synthesis of 4,4,4-trifluorobutyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate A1 Thionyl chloride (Commercially available, 3 equiv., 2 mmol) was added drop wise to 4,4,4-trifluorobutan-1-ol (2 mL). When the exothermic addition was finish, the reaction was stirred for 5 minutes and 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoic acid (Commercially available, 0.2 g, 0.7 mmol) was added. The solution was stirred at 70° C. for 2 hours. The reaction was cooled and quenched by addition of water. The aqeuous layer was extracted with ethyl acetate and washed with a saturated solution of sodium hydrogenocarbonate. After separation, the organic phase was dried and concentrated under vacuum to give 4,4,4-trifluorobutyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate A1 (0.22 g, 80%). Mp=118-119° C., 1H NMR (400 MHz, CDCl3) δ 8.32 (m, 2H), 8.12 (d, 1H), 7.78 (dd, 1H), 4.20 (m, 2H), 2.74 (m, 4H), 2.20 (m, 2H), 1.92 (m, 2H) ppm.
Reference： [1]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2013/87800, 2013, A1 Location in patent: Page/Page column 27
[2]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - US2014/371070, 2014, A1 Location in patent: Paragraph 0066; 0067
  • 4
  • [ CAS Unavailable ]
  • [ 188011-69-0 ]
  • [ 1443415-73-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In tetrahydrofuran at 0 - 20℃; for 0.333333h; II Example II: Synthesis of but-2-ynyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate A20 A stock solution of, 4-[(5-bromo-2-pyridyl) amino]-4-oxo-butanoic acid (Commercially available, 560mg) is prepared in 28.7mL THF. 0.7 mL of this solution is dispensed into each vial. Then a large excess of alcohol was added and distributed in an Alu24 rack (For the liquid: 0.3mL, for the solid: lOeq. dissolved into 0.3mL THF). In the present example, 0.3 mL of but-2-yn-l-ol was added in a vial. The vials are cooled down to 0°C and thionylcholoride is added with the multipette (20uL). The vials are stirred for 20 min at room temperature. The solvent was evaporated and a mixture of water (2ML) and ethyl acetate (2mL) was added. The phases are separated and the aqueous layer was extracted (x2) with ethyl acetate (2mL). The organic phases were collected and concentrated under vacuum. The samples were dissolved in 0.8mL of DMF in a 96DPW for the purification. The samples were purified by HPLC and analyse by LC-MS.
With thionyl chloride In tetrahydrofuran at 0 - 20℃; for 0.333333h; II Synthesis of but-2-ynyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate A20 Example II Synthesis of but-2-ynyl 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoate A20 A stock solution of, 4-[(5-bromo-2-pyridyl)amino]-4-oxo-butanoic acid (Commercially available, 560 mg) is prepared in 28.7 mL THF. 0.7 mL of this solution is dispensed into each vial. Then a large excess of alcohol was added and distributed in an Alu24 rack (For the liquid: 0.3 mL, for the solid: 10 eq. dissolved into 0.3 mL THF). In the present example, 0.3 mL of but-2-yn-1-ol was added in a vial. The vials are cooled down to 0° C. and thionylcholoride is added with the multipette (20 uL). The vials are stirred for 20 min at room temperature. The solvent was evaporated and a mixture of water (2 ML) and ethyl acetate (2 mL) was added. The phases are separated and the aqueous layer was extracted (*2) with ethyl acetate (2 mL). The organic phases were collected and concentrated under vacuum. The samples were dissolved in 0.8 mL of DMF in a 96DPW for the purification. The samples were purified by HPLC and analyse by LC-MS. The compounds A21 to A40 from table A were prepared, in parallel by the same method using the appropriate alcohol.
Reference： [1]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - WO2013/87800, 2013, A1 Location in patent: Page/Page column 27; 28
[2]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD; Syngenta (in: Sinochem Holdings) - US2014/371070, 2014, A1 Location in patent: Paragraph 0069; 0070; 0071
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