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[ CAS No. 3463-30-7 ] {[proInfo.proName]}

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Chemical Structure| 3463-30-7
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Product Details of [ 3463-30-7 ]

CAS No. :3463-30-7 MDL No. :MFCD00187828
Formula : C9H7N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PNWPAZGIVRZAER-UHFFFAOYSA-N
M.W : 189.17 Pubchem ID :605059
Synonyms :

Calculated chemistry of [ 3463-30-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.39
TPSA : 63.64 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) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.45
Log Po/w (XLOGP3) : 2.25
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 0.64
Log Po/w (SILICOS-IT) : -0.7
Consensus Log Po/w : 1.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.88
Solubility : 0.249 mg/ml ; 0.00132 mol/l
Class : Soluble
Log S (Ali) : -3.22
Solubility : 0.113 mg/ml ; 0.000599 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.927 mg/ml ; 0.0049 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 3463-30-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3463-30-7 ]

* 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 [ 3463-30-7 ]
  • Downstream synthetic route of [ 3463-30-7 ]

[ 3463-30-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 3463-30-7 ]
  • [ 17635-45-9 ]
YieldReaction ConditionsOperation in experiment
95% With hydrazine hydrate In ethanol at 70℃; for 4 h; General procedure: In a typical reaction, 5.0 mg of Pd-gCN (5.0 wtpercent of Pd) catalyst was added to the solution of 1.0 mM of nitroarene in ethanol (2 mL)and 2 mM (1.2 equiv. 0.07 mL) of 60percent of hydrazine hydrate. The mixture was placed into a 10 mL round-bottom flask at the reflux temperature (70° C) for the 4 h and then allowed to cool at room temperature. The resultant material was filtered and the filtrate was subjected to column chromatography over silica gel to obtain the corresponding products. For di-nitroarenes substrates 4.0 mM(2.4 equiv. 0.14 mL) of 60percent of hydrazine hydrate solution was used.
83% With tin(II) chloride hydrate In ethanol for 2 h; Reflux Synthesis of 1-(4-aminophenyl)-1H-pyrazole b
Compound a (5 mmol) was dissolved in ethanol (15 mL), then stannous chloride hydrate (10 eq.) was added, refluxed for 2 hrs, and cooled.
The pH of the solution was adjusted to weakly basic with saturated sodium bicarbonate solution, and then was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated to give compound b (0.66 g) in 83percent yield. Exact Mass (cal.): 159.0796; MS (ESI) m/e(M+1)+: 160.0879.
80% With ammonium chloride; zinc In ethanol; water for 0.5 h; Reflux Compound 11-b (1.0 g, 5.29 mmol) and ammonium chloride (0.7 g, 13.23 mmol) were dissolved in 50percent ethanol-water (20 mL). Zn-powder (0.9 g, 13.23 mmol) was then added. The mixture was refluxed for 30 minutes. After cooled to room temperature, the mixture was filtrated, and the filter cake was washed with ethanol (10 mL). The combined filtrate were concentrated under reduced pressure, and the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×3). The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give yellow solid 11-a (670 mg, yield: 80percent), which was used directly for the next step without purification. LC-MS (ESI): m/z=160 [M+H]+.
79.98% With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 0.5 h; Reflux To the reaction flask was added successively 1-(4-nitrophenyl)-1H-pyrazole (40.00 g, 211.45 mmol), ethanol (400 ml), 85percent hydrazine hydrate (37.36 g, 634.34 mmol) and 10percent palladium on carbon catalyst (3.38 g, 3.17 mmol) and the reaction was heated to reflux. After the reaction was refluxed for 0.5 hours, the reaction solution was cooled to room temperature, filtered to remove the palladium on carbon catalyst, concentrated under reduced pressure, to the residue was added water (300 ml), and extracted with ethyl acetate (3 × 500 ml), the organic layer was washed with saturated under brine (200 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, and the residue was purified by column chromatography (as eluent PE: EA = 1: 1 (v / v)), light yellow solid 26.92 g, yield 79.98percent.
1.5 g With palladium on activated charcoal; hydrogen In methanol at 20℃; for 16 h; 2 (2.0 g, 10.15 mmol), MeOH (40 mL). Pd/C (1.0 g). RT, hydrogen balloon pressure, 16h. Purification afforded 1.5 g of 3.of
1.7 g With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 16 h; [00264] To a stirred solution of compound 2 (2.4 g, 12.7 mmol) in EtOH (20 mL) at RT, was added 10percent Pd/C (50percent wet, 500 mg). The reaction mixture was stirred at RT under hydrogen (1 atmosphere pressure) for 16 h. The mixture was filtered through a pad of celite and the celite bed was washed with methanol (30 mL). The filtrate was concentrated under reduced pressure to afford compound 3 (1.7 g, 79percent over two steps) as colorless oil, which did not require further purification. H MR (400 MHz, DMSO-i: δ 8.18 (d, J = 2.0 Hz, 1H), 7.60 (d, J= 1.4 Hz, 1H), 7.42 (d, J = 8.8 Hz, 2H), 6.63 (d, J= 8.8 Hz, 2H), 6.42 (t, J= 1.9 Hz, 1H), 5.19 (s, 2H).

Reference: [1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1935 - 1946
[2] Applied Catalysis A: General, 2016, vol. 523, p. 31 - 38
[3] Patent: EP3159340, 2017, A1, . Location in patent: Paragraph 0086; 0091
[4] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0165; 0167
[5] Patent: CN105418590, 2016, A, . Location in patent: Paragraph 0152; 0153; 0154
[6] Tetrahedron, 2001, vol. 57, # 20, p. 4397 - 4403
[7] Gazzetta Chimica Italiana, 1956, vol. 86, p. 797,808
[8] Applied Spectroscopy, 1995, vol. 49, # 8, p. 1111 - 1119
[9] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1221 - 1227
[10] Patent: EP1612204, 2006, A1, . Location in patent: Page/Page column 23
[11] Patent: WO2016/73652, 2016, A1, . Location in patent: Page/Page column 64
[12] Turkish Journal of Chemistry, 2016, vol. 40, # 5, p. 729 - 741
[13] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 545 - 557
[14] Patent: WO2017/139274, 2017, A1, . Location in patent: Paragraph 00264
  • 2
  • [ 3463-30-7 ]
  • [ 25699-83-6 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 20, p. 4397 - 4403
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