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[ CAS No. 1128-56-9 ] {[proInfo.proName]}

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Product Details of [ 1128-56-9 ]

CAS No. :1128-56-9 MDL No. :MFCD00100520
Formula : C9H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :BQQFSUKXGGGGLV-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :594320
Synonyms :

Calculated chemistry of [ 1128-56-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.97
TPSA : 43.84 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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.52
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.62 mg/ml ; 0.00389 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.36 mg/ml ; 0.00851 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.56
Solubility : 0.444 mg/ml ; 0.00279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 1128-56-9 ]

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 [ 1128-56-9 ]

* 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 [ 1128-56-9 ]
  • Downstream synthetic route of [ 1128-56-9 ]

[ 1128-56-9 ] Synthesis Path-Upstream   1~18

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Reference: [1] ChemCatChem, 2015, vol. 7, # 16, p. 2433 - 2436
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YieldReaction ConditionsOperation in experiment
41% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 20℃; for 1 h; To a solution of 1-phenyl-3-amino-pyrazoline(7.4 g, 46 mmol) in dioxane (200 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (11.54 g, 50 mmol). After addition, the reaction was stirred at RT for 1 hour, then the resulting dark solution was filtered through a pad of Celite. The filtrate was acidified with 1N aqueous HCl (100 mL) and extracted with CH2Cl2 (50 mL). The organic layer was extracted with 1N aqueous HCl (50 mL). The combined aqueous layers were washed with CH2Cl2 (2.x.50 mL), then adjusted to pH12 with NaOH, followed by extraction with CH2Cl2 (3.x.100 mL). The combined CH2Cl2 extracts were washed with saturated NaCl (100 mL), dried (MgSO4), and concentrated under reduced pressure to give the title compound, 1-phenyl-3-amino-pyrazole as light orange solid (3.0 g, 41percent yield). LC/MS (method A): retention time=1.43 min, (M+H)+=160.
12.2 g
Stage #1: With chloranil In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 4.83333 h; Cooling with ice
Stage #2: With sodium hydroxide In 1,4-dioxane; water; N,N-dimethyl-formamide at 20℃; for 1.41667 h; Cooling with ice
To a solution of 1-phenyl-4,5-dihydro-1H-pyrazol-3-ylamine (50.0 g) in N,N-dimethylformamide (150 ml) and 1,4-dioxane (500 ml) was added 3,4,5,6-tetrachloro-1,4-benzoquinone (84.0 g) under ice-cooling over 20 minutes, and the mixture was stirred at room temperature for 4.5 hours.
To the reaction mixture was added a 2M aqueous solution of sodium hydroxide (400 ml) under ice-cooling over 25 minutes, and the mixture was stirred at room temperature for 1 hour.
The mixture was filtered through Celite to remove the insoluble substance, and eluted with ethyl acetate (250 ml*3), and then the filtrate was extracted with ethyl acetate (300 ml).
The resulting organic layer was sequentially washed with water (300 ml) and a saturated aqueous solution of sodium chloride (300 ml).
The separated aqueous layer was extracted twice with ethyl acetate (300 ml).
To the combined organic layer were added anhydrous sodium sulfate (50 g) and silica gel (50 g), and the mixture was stirred at room temperature for 1 hour.
This mixture was filtered with silica gel (100 g) on Celite, and subjected to elution with ethyl acetate (250 ml*3).
The filtrate was concentrated, and diisopropyl ether (500 ml) was added to the resulting residue, and the mixture was stirred at room temperature.
The insoluble substance was collected by filtration, washed twice with diisopropyl ether (100 ml), and dried under reduced pressure to give the titled compound (12.2 g).
1H-NMR (CDCl3) δ: 3.81 (br s, 2H), 5.85 (d, 1H, J=2.4 Hz), 7.16-7.19 (m, 1H), 7.38-7.40 (m, 2H), 7.55-7.57 (m, 2H), 7.69 (d, 1H, J=2.4 Hz).
Reference: [1] Bioorganic and medicinal chemistry, 2002, vol. 10, # 3, p. 817 - 827
[2] Patent: US4149005, 1979, A,
[3] Farmaco, Edizione Scientifica, 1985, vol. 40, # 11, p. 808 - 817
[4] Patent: US2006/154956, 2006, A1, . Location in patent: Page/Page column 9
[5] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 658,659; engl. Ausg. S. 650, 651
[6] Patent: US4149005, 1979, A,
[7] Patent: US4149005, 1979, A,
[8] Patent: US2013/85132, 2013, A1, . Location in patent: Paragraph 0680; 0681; 0682
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YieldReaction ConditionsOperation in experiment
80% With caesium carbonate; copper(ll) bromide In N,N-dimethyl-formamide at 190℃; for 0.333333 h; Microwave irradiation; Sealed tube 1 -phenyl- 1 H -pyrazol-3-amine 3-Amino-pyrazole (1 .0 g, 12.03 mmol), Cs2CO3 (3.92 g, 12.03 mmol), iodobenzene (3.68 g, 18.05 mmol), CuBr2 (0.268 g, 0.1 mmol), and DMF (4 ml_) were added to a 10-mL microwave vial. The vial was sealed and heated to 190 °C for 20 min (monitored by TLC). After cooling, the reaction mixture was diluted with saturated aqueous ammonium chloride and extracted with ethyl acetate (50 imL x 3). The organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography, eluting with 0-40percent ethyl acetate and petroleum benzine, afforded the desired product, 1 -phenyl-1 -/-pyrazol-3-amine, as a brown solid (1 .53 g, 80percent).
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 6, p. 2067 - 2070
[2] Patent: WO2015/172196, 2015, A1, . Location in patent: Paragraph 00225
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YieldReaction ConditionsOperation in experiment
85% With sodium ethanolate In ethanol at 150℃; for 2 h; Sealed tube; Microwave irradiation 3.6
3-Amino-1-phenyl-1H-pyrazole (11a)
A solution of phenylhydrazine hydrochloride (2d·HCl) (0.17 g, 1.2 mmol), 3-methoxyacrylonitrile (1a) (0.20 mL, 2.4 mmol) and NaOEt (0.41 g, 4.8 mmol) in dry EtOH (4 mL) was irradiated at 150 °C for 2 h in a sealed, pressure-rated Pyrex tube (10 mL) using a CEM Discover microwave synthesizer by moderating the initial power (150 W).
The mixture was cooled by passing a stream of compressed air through the microwave cavity and H2O was added (10 mL).
The aqueous layer was extracted with EtOAc (2*20 mL) and the organic extracts were combined, washed with brine, dried (MgSO4) and evaporated in vacuo.
Purification by column chromatography on silica, eluting with hexane/EtOAc (1:3 v/v), gave the title compound (0.19 g, 85percent) as a yellow solid, mp 90-92 °C (lit.
44
mp 91 °C) (found: 159.0796. C9H9N3 [M] requires 159.0796); FTIR (KBr)/cm-1 νmax 3477 (NH), 3297 (NH), 1490, 1415, 1367, 1172; 1H NMR (400 MHz; DMSO-d6) δ 8.13 (1H, d, J 2.4, H-5), 7.64 (2H, d, J 7.7, H-2'/H-6'), 7.39 (2H, t, J 7.7, H-3'/H-5'), 7.11 (1H, t, J 7.7, H-4'), 5.74 (1H, d, J 2.4, H-4), 5.09 (2H, br s, exch. D2O, NH2); 13C NMR (126 MHz; DMSO-d6) δ 157.5 (C), 140.4 (C), 129.7 (CH), 128.2 (CH), 124.3 (CH), 116.8 (CH), 96.8 (CH); LRMS (EI) m/z (rel intensity) 159 (M<ce:glyph name="rad"/>+, 100), 158 ([M-1]+, 30), 131 ([M-N2]<ce:glyph name="rad"/>+, 13), 104 (16), 92 (8), 84 (27), 77 (Ph+, 29).
Reference: [1] Tetrahedron, 2013, vol. 69, # 39, p. 8429 - 8438
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YieldReaction ConditionsOperation in experiment
48% With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 100℃; for 16 h; Potassium te/ -butoxide (1 1 .9 g, 106.3 mmol) was dissolved in tBuOH (1 OOmL) and the solution was heated to 100 °C. Phenyl hydrazine (5 g, 46.2 mmol) and 3-ethoxy acrylonitrile (4.5 g, 46.2 mmol) were sequentially added and heating continued for 16 h. The mixture was concentrated in vacuo. The residue obtained was partitioned between water (500 mL) and ethyl acetate (500 mL). The organic extract was washed with water (250 mL), brine (250 mL), dried (Na2S04) and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using 25percent EtOAc-hexanes eluent to give 1 - phenyl-1 H-pyrazol-3-amine as a pale brown solid (3.5 g, 48percent). 1H NMR (400 MHz, CDCI3): δ = 7.69 (s, 1 H), 7.57 (d, J= 8.0 Hz, 2H), 7.41 (d, J= 8.0 Hz, 2H), 7.2 (t, J = 7.6 Hz, 1 H), 5.85 (s, 1 H), 3.83 (br.s., 2H). LCMS (m/z): 160.3 (M+1 )+.
Reference: [1] Patent: WO2016/131098, 2016, A1, . Location in patent: Page/Page column 135; 136
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Reference: [1] Patent: WO2004/37794, 2004, A1, . Location in patent: Page 61-62
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Reference: [1] Patent: WO2004/37794, 2004, A1, . Location in patent: Page 62-64
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Reference: [1] Patent: WO2015/193506, 2015, A1, . Location in patent: Page/Page column 53
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Reference: [1] Patent: US4149005, 1979, A,
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Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1265 - 1266
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Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1265 - 1266
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Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1265 - 1266
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Reference: [1] ChemCatChem, 2015, vol. 7, # 16, p. 2433 - 2436
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Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1265 - 1266
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Reference: [1] Journal of the Chemical Society, 1954, p. 408,411[2] Journal of the Chemical Society, 1955, p. 3470,3473
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Reference: [1] Journal of the Chemical Society, 1954, p. 408,411[2] Journal of the Chemical Society, 1955, p. 3470,3473
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Reference: [1] Journal of the Chemical Society, 1954, p. 408,411[2] Journal of the Chemical Society, 1955, p. 3470,3473
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Reference: [1] Journal of the Chemical Society, 1954, p. 408,411[2] Journal of the Chemical Society, 1955, p. 3470,3473
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