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[ CAS No. 417721-69-8 ] {[proInfo.proName]}

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Chemical Structure| 417721-69-8
Chemical Structure| 417721-69-8
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Product Details of [ 417721-69-8 ]

CAS No. :417721-69-8 MDL No. :MFCD08741521
Formula : C5H4ClIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :BWMULFKDCVPGNF-UHFFFAOYSA-N
M.W : 254.46 Pubchem ID :22936596
Synonyms :

Calculated chemistry of [ 417721-69-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.37
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 1.76
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.236 mg/ml ; 0.000928 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 1.55 mg/ml ; 0.00609 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.148 mg/ml ; 0.000581 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.06

Safety of [ 417721-69-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 417721-69-8 ]

* 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 [ 417721-69-8 ]
  • Downstream synthetic route of [ 417721-69-8 ]

[ 417721-69-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 868733-96-4 ]
  • [ 417721-69-8 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: at 100℃; for 0.166667 h;
Stage #2: With sodium hydroxide In water
A suspension of (4-chloro-3-iodo-pyridin-2-yl)-carbamic acid tert-butyl ester (5.6 g, 15.8 mmol) in 48percent hydrobromic acid was heated at 100° C. for 10 min to give a clear solution. The mixture was cooled, treated with crushed ice and made basic with 6 M NaOH. The precipitated product was collected by vacuum filtration, washed with H2O and sucked partially on the funnel to give a white solid. The product was dissolved in THF and the solution dried over MgSO4 and concentrated in vacuo to give the title compound (3.7 g, 93percent) as a white solid. 1H NMR (DMSO-d6) δ 7.84 (d, 1H, J=5.1 Hz), 6.73 (d, 1H, J=5.6 Hz), 6.51 (br s, 2H); MS (ESI+): m/z 254.97 (M+H)+.
93% With hydrogen bromide In water at 100℃; for 0.166667 h; Inert atmosphere General procedure: the previously synthetized compound (4.2 g, 11.86mmol) was dissolved into HBr 48percent (50 mL) and the solution was heated at 100°Cfor 10 minutes. The mixture was cooled at room temperature andwas poured with stirring into ice and water (100 mL). The resulting suspensionwas alkalinized with a 6M solution of NaOH (100 mL). The resulting solid wasfiltered, washed with water and dissolved into THF. The organic phase was driedover MgSO4, filtered andconcentrated under reduced pressure.The aminopyridine 2k was obtained as a beigesolid (3.3 g, 93percent) without further purification. Spectral data were inagreement with literature.
90%
Stage #1: at 20℃; for 3 h;
Stage #2: With sodium hydroxide In water
A solution of aqueous HBr (48percent, 10 mL, 13.26 mmol) was added to tert-butyl (4- chloro-3-iodopyridin-2-yl)carbamate (4.7 g, 13.26 mmol) and the suspension was stirred at RT for 3h. The reaction mixture was diluted with water (40 ml), basified with 2N NaOH and the resultant suspension was filtered, washed with water (4 x 1 mL) and dried to afford 4-chloro-3- iodopyridin-2-amine as white solid (3.05 g, 90percent yield). MS (ESI) m/z: 254.9 (M+H+).
65% With methoxybenzene; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 1.5 h; Intermediate 3 4-Chloro-3-iodopyridin-2-amine [0041] A 250 mL round bottom flask was charged with tert-butyl (4-chloro-3-iodopyridin-2-yl)carbamate (4.5 g, 12.69 mmol) and dissolved in DCE (50.8 mL). To that stirring solution was added anisole (2.77 mL, 25.4 mmol) followed by TFA (14.67 mL, 190 mmol) at rt. After 1.5 hours, LCMS showed clean and complete consumption of the starting material to a large peak with the desired mass (m/z=254[M+H]+Methanol/Water/TFA Phenomenex Luna C18, 30×2 mm, 3u ES+/−). The mixture was concentrated under reduced pressure into a collection bulb that was pretreated with 3.0 M NaOH. The crude mixture was then redissolved in toluene to aid in the removal of any volatiles. The crude solid was then diluted with EtOAc and sat'd sodium bicarbonate. The mixture was stirred for 15 min. The contents of the flask were transferred into a separatory funnel where the aqueous layer was extracted twice with EtOAc and discarded. The combined organics were washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. The crude material was dissolved in a small amount of ethanol and then heated with a heat gun. The mixture was let sit and then after 5 min cooled in an acetone dry ice bath. The solids were sonicated and collected by filtration. The mother liquor was concentrated and the above procedure was repeated. 4-chloro-3-iodopyridin-2-amine (2.1 g, 65percent yield) was collected as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.88 (d, J=5.3 Hz, 1H), 6.74 (d, J=5.3 Hz, 1H), 5.20 (br. s., 2H).

Reference: [1] Molecules, 2012, vol. 17, # 9, p. 10683 - 10707,25
[2] Molecules, 2012, vol. 17, # 9, p. 10683 - 10707
[3] Patent: US2005/245530, 2005, A1, . Location in patent: Page/Page column 46
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 5, p. 1251 - 1254
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 114 - 120
[6] Patent: WO2011/139891, 2011, A1, . Location in patent: Page/Page column 54-55
[7] Patent: US2013/245042, 2013, A1, . Location in patent: Paragraph 0041
[8] Patent: WO2014/81617, 2014, A1, . Location in patent: Page/Page column 69-70
  • 2
  • [ 19798-80-2 ]
  • [ 417721-69-8 ]
Reference: [1] Patent: WO2011/139891, 2011, A1,
[2] Molecules, 2012, vol. 17, # 9, p. 10683 - 10707,25
[3] Molecules, 2012, vol. 17, # 9, p. 10683 - 10707
[4] Patent: US2013/245042, 2013, A1,
[5] Patent: WO2014/81617, 2014, A1,
[6] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 114 - 120
  • 3
  • [ 130721-78-7 ]
  • [ 417721-69-8 ]
Reference: [1] Patent: WO2011/139891, 2011, A1,
[2] Molecules, 2012, vol. 17, # 9, p. 10683 - 10707,25
[3] Molecules, 2012, vol. 17, # 9, p. 10683 - 10707
[4] Patent: US2013/245042, 2013, A1,
[5] Patent: WO2014/81617, 2014, A1,
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