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[ CAS No. 914106-26-6 ] {[proInfo.proName]}

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Chemical Structure| 914106-26-6
Chemical Structure| 914106-26-6
Structure of 914106-26-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 914106-26-6 ]

CAS No. :914106-26-6 MDL No. :MFCD09025674
Formula : C7H3ClIN Boiling Point : -
Linear Structure Formula :- InChI Key :WUNSVSXKDMQXSB-UHFFFAOYSA-N
M.W :263.46 Pubchem ID :16659396
Synonyms :

Calculated chemistry of [ 914106-26-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.88
TPSA : 23.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 3.25
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.94
Log Po/w (SILICOS-IT) : 3.41
Consensus Log Po/w : 2.89

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.96
Solubility : 0.0286 mg/ml ; 0.000108 mol/l
Class : Soluble
Log S (Ali) : -3.42
Solubility : 0.0994 mg/ml ; 0.000377 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.05
Solubility : 0.0234 mg/ml ; 0.0000887 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.01

Safety of [ 914106-26-6 ]

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 [ 914106-26-6 ]

* 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 [ 914106-26-6 ]
  • Downstream synthetic route of [ 914106-26-6 ]

[ 914106-26-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 914106-25-5 ]
  • [ 914106-26-6 ]
YieldReaction ConditionsOperation in experiment
91% for 4 h; Heating / reflux 4-Chloro-3-iodobenzonitrile (60f). A mixture of aldoxime 59 (5.65 g, 20.0 mmol) in acetic anhydride (10 mL) was refluxed for 4 h. The reaction mixture was poured into ice-water and stirred for 1 h. The product was filtered off as a light yellow solid (4.79 g, 91percent): mp 91-93 °C; 1H NMR δ 8.49 (d, J = 2.2 Hz, 1H), 7.90 (dd, J = 8.2 and 2.2 Hz, 1H), 7.79 (d, J = 8.2 Hz, 1H); HPLC (Method B) tR 6.24 min (91.75 area percent at 254 nm). Anal. (C7H3CllN) C, H, N, Cl, l.; Reagents and conditions: (a) fuming HNO3, H2SO4; (b) Fe, AcOH, EtOH; (c) NaNO2, aq. HCl, then CuCl; (d) NalO4, l2, AcOH, AC2O, H2SO4; (e) NH2OH HCl, Py, EtOH (f) Ac2O; (g) TMSA, Pd2Cl2(PPh3)2, Cul, Et3N; (h) TMSA, PPh3, Pd(PPh3)4, Cul, piperidine; (j) 2-methyl-3-butyn-2-ol, Pd2Cl2(PPh3)2, Cul, Et3N; (k) 2-methyl-3-butyn-2-ol, 10percent Pd/C, PPh3, Cul, aq. K2CO3/DME; (I) Cs2CO3, aq. CH3CN or MeOH; (m) NaH, toluene.; A second general method is depicted in Scheme 2 immediately hereinabove and comprises the cycloaddition of cyanophenylacetylenes 51 and benzaldehyde chlorooximes 52 in the presence of bis(tributyltin) oxide, see Moriya, O., et al., J. Chem. Soc., Perkin Trans., 1, 413-417 (1994); Moriya, O., et al., J. Chem. Soc., Chem. Commun., 17-18 (1991), or triethylamine, see Thomsen, l., et al., Acta Chem. Scand. (B), 319-313 (1988), in nonpolar solvents to give isoxazole dinitriles 53a-h,k-s and bromonitrile 53i. The latter was treated with copper(I) cyanide to give dinitrile 53j. See Friedman. L., et al., J. Org. Chem., 26, 2522-2524 (1961). This method also afforded alternate routes to dinitriles 50a,b,g, k prepared by the first method as provided in Scheme 1. The phenylacetylene synthons 51a-g were prepared as shown in Scheme 3 below. Starting materials 60a,e,g were commercially available. Nitration of 60a gave 60b. See Borsche, W., L., et al., Chem. Ber., 49, 2222-2243 (1916). The latter was reduced to aniline 56, see Blanksma, J. J., et al., Recl. Trav. Chim. Pays-Bas, 66, 365-373 (1947), which underwent diazotization followed by treatment with copper(l) chloride to give chlorobenzene 60c. Triflate 60d was prepared by treatment of 4-bromo-3-hydroxybenzonitrile with triflic anhydride. The preparation of aryl iodide 60f began with the known transformation of aldehyde 57 to iodo derivative 58. See Lulinski, P., et al., Bull. Chem. Soc. Jpn., 73(4), 951-956 (2000). Treatment of 58 with hydroxylamine hydrochloride gave aldoxime 59, which was dehydrated to give nitrile 60f using acetic anhydride. The aryl halides or triflates 60a-g were treated with (trimethylsilyl)acetylene, see Roesch. K. R., et al., J. Org. Chem., 66, 412-420 (2001), or with 2-methyl-3-butyn-2-ol, see Bleicher, L. S., et al., J. Org. Chem., 63, 1109-1118 (1998), to give intermediates 61a-f or 62a-f, respectively, of which 61a,d and 62a have been reported previously. See Dirk. S. M., et al., Tetrahedron, 59(3), 287-293 (2003); Bleicher, L. S., et al., J. Org. Chem., 63, 1109-1118 (1998). The acetylenes 51 (of which 51a,e were known previously), see Blackburn, B. K., et al., J. Med. Chem., 40(5), 717-729 (1997); Dulog, L., et al., Liebigs Ann. Chem., 9, 1663-1671 (1995), were obtained by the treatment of intermediates 61 or 62 with cesium carbonate in acetonitrile or sodium hydride in toluene, respectively. See Bleicher, L. S., et al., J. Org. Chem., 63, 1109-1118 (1998). The use of cesium carbonate in acetonitrile was introduced for the deprotection of intermediates 61 after the treatment of compound 61b with potassium carbonate in methanol, see Blackburn, B. K., et al., J. Med. Chem., 40(5), 717-729 (1997), failed to give product 51b. The pathway using 2-methyl-3-butyn-2-ol provided more economical preparations of all phenylacetylenes 51 except nitro analog 51b.
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2468 - 2485
[2] Patent: EP1719767, 2006, A1, . Location in patent: Page/Page column 24-26
  • 2
  • [ 276866-90-1 ]
  • [ 914106-26-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2468 - 2485
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