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[ CAS No. 29241-62-1 ] {[proInfo.proName]}

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Chemical Structure| 29241-62-1
Chemical Structure| 29241-62-1
Structure of 29241-62-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 29241-62-1 ]

CAS No. :29241-62-1 MDL No. :MFCD01927098
Formula : C6H3BrClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DXEUARPQHJXMII-UHFFFAOYSA-N
M.W : 236.45 Pubchem ID :285433
Synonyms :

Calculated chemistry of [ 29241-62-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.91
TPSA : 50.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : 2.08
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.283 mg/ml ; 0.0012 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.459 mg/ml ; 0.00194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.316 mg/ml ; 0.00134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 29241-62-1 ]

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 [ 29241-62-1 ]

* 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 [ 29241-62-1 ]
  • Downstream synthetic route of [ 29241-62-1 ]

[ 29241-62-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 41668-13-7 ]
  • [ 29241-62-1 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: for 3 h; Heating / reflux
Stage #2: at 0℃; for 2 h;
8B. 5-Bromo-6-chloro-nicotinic acid: To 8A (10 g, 45 mmol) was added tetra-methylammonium chloride (5.4 g, 49 mmol) and phosphorous oxychloride (20 mL) and the reaction was heated at reflux for 3 h. The reaction was poured onto ice and stirred 2 h. The solid was filtered off, dissolved in EtOAc (300 mL) and dried (Na2SO4). After filtration and concentration, 10.5g (97percent) of 8B as a pink solid was collected. 1HNMR (400 MHz, DMSO-d6) δ: 8.53 (d, J = 2.02 Hz, 1H) 8.85 (d, J = 2.02 Hz, 1 H) 13.57 (s, 1 H).
Reference: [1] Patent: WO2007/70818, 2007, A1, . Location in patent: Page/Page column 103
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4892 - 4909
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9874 - 9896
  • 2
  • [ 17282-03-0 ]
  • [ 29241-62-1 ]
Reference: [1] Patent: US4317913, 1982, A,
[2] Patent: US2008/85906, 2008, A1, . Location in patent: Page/Page column 16
  • 3
  • [ 5006-66-6 ]
  • [ 29241-62-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4892 - 4909
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9874 - 9896
[3] Patent: WO2007/70818, 2007, A1,
  • 4
  • [ 5006-66-6 ]
  • [ 29241-62-1 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 1, p. 116 - 133
  • 5
  • [ 29241-62-1 ]
  • [ 74-88-4 ]
  • [ 78686-77-8 ]
YieldReaction ConditionsOperation in experiment
94.7% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; Step 1: Methyl 5-bromo-6-chloronicotinate (61). A mixture of 5-bromo-6- chloronicotinic acid 60 (0.2 g, 0.84 mmol), K2C03 (0.3 g, 2.1 mmol) and methyl iodide (0.178 g, 1.2 mmol) in DMF (10 mL) was stirred for 16 h at RT. After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 20 mL). The combined organic extracts were washed with saturated aqueous NaHC03 solution (20 mL), brine (2 x 20 mL) and dried (Na2S04) and concentrated to afford ester 61 (0.2 g, 94.7percent).
Reference: [1] Patent: WO2017/4608, 2017, A1, . Location in patent: Paragraph 0183
  • 6
  • [ 29241-62-1 ]
  • [ 18107-18-1 ]
  • [ 78686-77-8 ]
YieldReaction ConditionsOperation in experiment
74% at 0℃; for 1 h; Example 18; JV-Hydroxy-6-methoxy-5 -(pyridin-3 -ylethynyl)pyridine-3 -carboxamide; A. Methyl 5-bromo-6-chloropyridine-3-carboxylate; To a 0 0C solution of S-bromo-β-chloronicotinic acid (1.0 g, 4.2 mmol) in methanol :benzene (1 :1) (50 mL) was added trimethylsilyldiazomethane as a 2N solution in hexanes (3.2 mL, 6.5 mmol). The reaction was stirred for 60 min. The reaction mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate (40 mL), washed with water (10 mL x 2). The aqueous layer was extracted with ethyl acetate (50 mL x 2) and the combined organic layers were washed with brine solution (50 mL), dried over anhydrous MgSO4 and evaporated under reduced pressure to provide the crude compound. The crude compound was purified through a filter column (Silica gel, 100-200 mesh) to provide methyl 5-bromo-6-chloropyridine-3-carboxylate as an off-white solid (0.078 g, 74percent). LC-MS: [M+H] + 251. 1H NMR (400 MHz, CDCl3) δ: ppm 9.00 (s, IH) 8.40 (s, IH), 3.90 (s, 3H).
Reference: [1] Patent: WO2010/100475, 2010, A1, . Location in patent: Page/Page column 74-75
  • 7
  • [ 67-56-1 ]
  • [ 29241-62-1 ]
  • [ 78686-77-8 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 18, p. 3533 - 3537
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 9874 - 9896
[3] ChemMedChem, 2015, vol. 10, # 1, p. 116 - 133
  • 8
  • [ 29241-62-1 ]
  • [ 78686-77-8 ]
Reference: [1] Journal of Chemical & Engineering Data, 1981, vol. 26, # 3, p. 332 - 333
  • 9
  • [ 186581-53-3 ]
  • [ 29241-62-1 ]
  • [ 78686-77-8 ]
Reference: [1] Journal of Chemical & Engineering Data, 1981, vol. 26, # 3, p. 332 - 333
  • 10
  • [ 29241-62-1 ]
  • [ 93349-99-6 ]
Reference: [1] ChemMedChem, 2015, vol. 10, # 1, p. 116 - 133
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