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[ CAS No. 344331-90-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 344331-90-4
Chemical Structure| 344331-90-4
Chemical Structure| 344331-90-4
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Product Details of [ 344331-90-4 ]

CAS No. :344331-90-4 MDL No. :MFCD07367929
Formula : C10H13BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WZDMEUOIVUZTPB-UHFFFAOYSA-N
M.W : 273.13 Pubchem ID :13040380
Synonyms :

Calculated chemistry of [ 344331-90-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.18
TPSA : 51.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 2.78
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.132 mg/ml ; 0.000482 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0841 mg/ml ; 0.000308 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.83
Solubility : 0.0406 mg/ml ; 0.000149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.6

Safety of [ 344331-90-4 ]

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 [ 344331-90-4 ]

* 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 [ 344331-90-4 ]
  • Downstream synthetic route of [ 344331-90-4 ]

[ 344331-90-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 344331-90-4 ]
  • [ 19798-81-3 ]
Reference: [1] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 2
  • [ 19798-81-3 ]
  • [ 24424-99-5 ]
  • [ 344331-90-4 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In dichloromethane at 20℃; for 72 h; Step 1. Preparation of te/f-butyl 6-bromopyridin-2-ylcarbamateTo a solution of 6-bromopyridin-2-amine (3 g, 17.34 mmol), triethylamine (3.14 mL, 22.54 mmol) and DMAP (0.424 g, 3.47 mmol) in DCM (24 mL) was added slowly a solution of BOC-anhydride (4.83 mL, 20.81 mmol) in DCM (6 mL). The reaction mixture was stirred at ambient temperature for -24 hr. The mixture was diluted with water, brine and EtOAc. The separated aqueous layer was extracted with EtOAc. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography providing te/f-butyl 6-bromopyridin-2- ylcarbamate as a white solid. Yield: 1.67 g. LCMS (m/z): 274.9 [M+H]+; Retention time = 0.95 min.
67% With dmap; triethylamine In dichloromethane at 20℃; for 10 h; To a solution of6-bromopyridin-2-amine (1.0 g,5.78 mmol),di-tert-butyl dicarbonate25 (1.4 g,6.2 mmol)in DCM (10 mL)were added triethylamine (1.58 mL,11.91 mmol)and 4~dimellrylaminopyridine (140 mg,1.17 mmol). The reaction mixture was stirred at room temperature for 10 h and concentrated in vacuo. The crude residue was purified by silica gelcolumn chromatography (petroleum ether/Et0Ac=10: 1)to give the title compound (1.1 g,67percent)as a white solid. 1HNMR (400 MHz,CDCl3)8 7.55-7.48 (m,1H),7.31 (d,J= 8.0 Hz,1H),7.19 (t,J = 4.0 Hz,2H),1.44 (s,9H).
50% With dmap; triethylamine In dichloromethane at 20℃; for 18 h; 62 g (284 mmol) of di-tert-butyl dicarbonate diluted in 200 ml of dichloromethane are added dropwise to A solution of 49.2 g (284 mmol) of 2-amino-6- bromopyridine, 43.4 ml (312 mmol) of triethylamine and 3.5 g (28.4 mmol) of 4-DIMETHYLAMINOPYRIDINE in 400 ml of dichloromethane. The reaction medium is stirred at room temperature for 18 hours. After addition of water and extraction with dichloromethane, the organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin- layer chromatography on silica eluted with a 95/5 heptane/ethyl acetate mixture. 39 g (50percent) of tert-butyl (6-bromopyrid-2-yl) carbamate are obtained in the form of a white solid.
50% With triethylamine In dichloromethane at 20℃; for 18 h; Example 6: 3-{4-[6-(3-Heptyl-l-πtethylureido)pyrid-2- yl]phenyl}propanoic acid; a. text-Butyl (6-bromopyrid-2-yl)carbamate; 62 g (284 mmol) of di-tert-butyl dicarbonate diluted in 200 ml of dichloromethane are added dropwise to a solution of 49.2 g (284 mmol) of 2-amino-6- bromopyridine, 43.4 ml (312 mmol) of triethylamine and 3.5 g (28.4 mmol) of 4-dimethylaminopyridine in 400 ml of dichloromethane. The reaction medium is stirred at EPO <DP n="41"/>room temperature for 18 hours. After addition of water and extraction with dichloromethane, the organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 95/5 heptane/ethyl acetate mixture. 39 g (50percent) of tert-butyl (β-bromopyrid-2-yl) carbamate are obtained in the form of a white solid.
21% With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Step G; Commercially available 2-amino-6-bromo-pyridine (4.25 g, 24.6 mmol) was dissolved in dichloromethane (50 mL) and N,N'-diisopropylethylamine (5.25 mL, 30.7 mmol) and 4-dimethylaminopyridine (0.1 g. 1.23 mmol) was added. After the addition of a solution of di-tert-butyl dicarbonate (5.9 g, 27 mmol) in dichloromethane (15 mL), the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane (100 mL) and washed with 10 percent citric acid (50 mL) and brine (50 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a white solid (2.15 g, 32 percent). Washing the column with ethylacetate/ n-heptane (10/90) afforded the corresponding bis-Boc-derivative as a white solid (1.95 g. 21 percent). 1H-NMR (400 MHz, CDCl3): d = 1.52 (s, 9H), 7.13 (d, 1H), 7.27 (br-s, 1H), 7.51 (t, 1H), 7.90 (d, 1H) Bis-Boc derivative: 1H-NMR (400 MHz, CDCl3): d = 1.48 (s, 18H), 7.27 (d, 1H), 7.40 (d. 1H), 7.60 (t, 1H)

Reference: [1] Patent: WO2012/101066, 2012, A1, . Location in patent: Page/Page column 77
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8709 - 8715
[3] Patent: WO2017/205536, 2017, A2, . Location in patent: Page/Page column 193; 194
[4] Patent: WO2004/113331, 2004, A1, . Location in patent: Page 68
[5] Patent: WO2006/53791, 2006, A2, . Location in patent: Page/Page column 39-40
[6] Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 1886 - 1900
[7] Patent: EP2311823, 2011, A1, . Location in patent: Page/Page column 31; 32
[8] Patent: US2011/28492, 2011, A1, . Location in patent: Page/Page column 20-21
[9] Patent: WO2012/101065, 2012, A2, . Location in patent: Page/Page column 125
[10] Patent: WO2012/101063, 2012, A1, . Location in patent: Page/Page column 92
[11] Patent: WO2012/101064, 2012, A1, . Location in patent: Page/Page column 132
  • 3
  • [ 21190-87-4 ]
  • [ 75-65-0 ]
  • [ 344331-90-4 ]
YieldReaction ConditionsOperation in experiment
66% for 2 h; Heating / reflux Example 66: Tert-butyl (6-bromopyridin-2-yl)carbamate; Diphenylphosphoryl azide (10.7 mL, 50 mmol, 1.0 equiv) was added to a solution of 6- bromopyridine-2-carboxylic acid (10.0 g, 50 mmol, 1.0 equiv) and triethylamine (6.8 mL, 50 mmol, 1.0 equiv) in anhydrous ferf-butyl alcohol (250 mL). The reaction mixture was refluxed for 2 hours, concentrated in vacuo and diluted with ethyl acetate. The organic layers were washed with 0.5 M sodium citrate buffer (pH = 4.5), saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified over silica (Biotage Horizon silica gel 40M column) and eluted with 8percent ethyl acetate in hexanes which provided a light yellow solid (8.9 g, 66percent yield): 1H NMR (400 MHz, DMSO-d6) δ 10.13 (s, 1 H), 7.78 (d, J = 8.1 Hz,1H), 7.65 (t, J = 8.0Hz, 1H), 7.20 (d, J = 7.6Hz, 1H), 1.45 (s, 9H); LCMS (ESI+) forC10H13BrN2O2 m/z 295/297 (M + Na)+.
Reference: [1] Patent: WO2006/43145, 2006, A1, . Location in patent: Page/Page column 104
[2] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
  • 4
  • [ 19798-81-3 ]
  • [ 75-44-5 ]
  • [ 75-65-0 ]
  • [ 344331-90-4 ]
Reference: [1] Patent: US2013/5981, 2013, A1, . Location in patent: Page/Page column 6
  • 5
  • [ 19798-81-3 ]
  • [ 24424-99-5 ]
  • [ 870703-61-0 ]
  • [ 344331-90-4 ]
YieldReaction ConditionsOperation in experiment
32% With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Step GCommercially available 2-amino-6-bromo-pyridine (4.25 g, 24.6 mmol) was dissolved in dichloromethane (50 mL) and N,N'-diisopropylethylamine (5.25 mL, 30.7 mmol) and 4-dimethylaminopyridine (0.15 g, 1.23 mmol) was added. After the addition of a solution of di-tert-butyl dicarbonate (5.9 g, 27 mmol) in dichloromethane (15 mL), the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane (100 mL) and washed with 10percent citric acid (50 mL) and brine (50 mL). The organic phase was separated, dried over Na2SO4, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a white solid (2.15 g, 32percent). Washing the column with ethylacetate/n-heptane (10/90) afforded the corresponding bis-Boc-derivative as a white solid (1.95 g, 21percent).1H-NMR (400 MHz, CDCl3): δ=1.52 (s, 9H), 7.13 (d, 1H), 7.27 (br-s, 1H), 7.51 (t, 1H), 7.90 (d, 1H)Bis-Boc derivative:1H-NMR (400 MHz, CDCl3): δ=1.48 (s, 18H), 7.27 (d, 1H), 7.40 (d, 1H), 7.60 (t, 1H)
32% With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Commercially available 2-amino-6-bromo-pyridine (4.25 g. 24.6 mmol) was dissolved in dichloromethane (50 mL) and N.N'-diisopropylethylamine (5.25 mL, 30.7 mmol) and 4- dimethylaminopyridine (0.15 g, 1.23 mmol) was added. After the addition of a solution of di- tert-butyl dicarbonate (5.9 g, 27 mmol) in dichloromethane ( 1 5 mL), the mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane ( 100 mL) and washed with 10 percent citric acid (50 mL) and brine (50 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents were removed. The residue was purified by chromatography on silica using ethylacetate/n-heptane (5/95) to afford the title compound as a white solid (2.15 g, 32 percent). Washing the column with ethylacetate/ n-heptane ( 10/90) afforded the corresponding bis-Boc -derivative as a white solid (1.95 g, 21 percent).-NMR (400 MHz, CDC13): d = 1.52 (s, 9H), 7.13 (d, 1H), 7.27 (br-s, 1 II), 7.51 (t, 1H), 7.90 (d. I l l )Bis-Boc derivative:-NMR (400 MHz, CDC13): d = 1.48 (s, 18H), 7.27 (d, 1H), 7.40 (d, lH), 7.60 (t, 1H)
Reference: [1] Patent: US2011/92537, 2011, A1, . Location in patent: Page/Page column 29-30
[2] Patent: WO2011/45383, 2011, A2, . Location in patent: Page/Page column 65
[3] Patent: WO2009/115557, 2009, A2, . Location in patent: Page/Page column 100-101
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  • [ 870703-61-0 ]
  • [ 344331-90-4 ]
Reference: [1] Patent: WO2009/115557, 2009, A2, . Location in patent: Page/Page column 100-101
  • 7
  • [ 19798-81-3 ]
  • [ 344331-90-4 ]
Reference: [1] Patent: WO2009/115557, 2009, A2,
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