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[ CAS No. 69843-13-6 ] {[proInfo.proName]}

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Chemical Structure| 69843-13-6
Chemical Structure| 69843-13-6
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Product Details of [ 69843-13-6 ]

CAS No. :69843-13-6 MDL No. :MFCD05667135
Formula : C4H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :LBGSWBJURUFGLR-UHFFFAOYSA-N
M.W :97.12 Pubchem ID :4770990
Synonyms :

Calculated chemistry of [ 69843-13-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.89
TPSA : 43.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.88
Log Po/w (XLOGP3) : -0.45
Log Po/w (WLOGP) : 0.01
Log Po/w (MLOGP) : -0.68
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : -0.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.69
Solubility : 20.0 mg/ml ; 0.205 mol/l
Class : Very soluble
Log S (Ali) : 0.0
Solubility : 96.0 mg/ml ; 0.989 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.35
Solubility : 43.0 mg/ml ; 0.443 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 69843-13-6 ]

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 [ 69843-13-6 ]

* 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 [ 69843-13-6 ]
  • Downstream synthetic route of [ 69843-13-6 ]

[ 69843-13-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 3994-50-1 ]
  • [ 69843-13-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In methanol at 70℃; Example 317
3-amino-6-bromo-N-(1-methyl-1H-pyrazol-4-yl)picolinamide 317
1-Methyl-4-nitro-1H-pyrazole (1.62 g, 12.7 mmol) was dissolved in methanol (250 mL) and hydrogenated on H-Cube at 60 bar hydrogen pressure and 70° C. to give 1-methyl-1H-pyrazol-4-amine (1.23 g, 99percent).
To a 100 mL round bottom flask containing 1-methyl-1H-pyrazol-4-amine (700 mg, 7.0 mmol), 3-amino-6-bromopicolinic acid (1.86 g, 8.5 mmol) and PyBop (4.12 g, 8.0 mmol) was added methylene chloride (30 mL) and diisopropylethylamine (3.8 mL, 21.6 mmol).
The reaction mixture was stirred for 24 hr at room temperature and the reaction was monitored by LCMS.
Upon completion of the reaction, the solvent was distilled off and the crude material was purified via flash chromatography, heptane/ethyl acetate 0percent to 100percent to afford a yellow solid.
A fraction of it was purified via reverse phase HPLC to afford 317. 1H NMR (400 MHz, DMSO) δ 10.25 (s, 1H), 8.03 (s, 1H), 7.70 (s, 1H), 7.43 (d, J=8.7 Hz, 1H), 7.19 (d, J=8.7 Hz, 1H), 7.02 (br, 2H), 3.81 (s, 3H). MS (ESI) m/z: 296.0/298.0 [M+H+].
99% With 50% palladium on charcoal; hydrogen In methanol A par flask was charged with 1-methyl-4-nitro-1H-pyrazole 15 (5.3 g, 41.0 mmol) and methanol (70 mL) followed by addition of Pd-C (50percent w/w, 2.70 g). The flask was evacuated under vacuum and then purged with hydrogen. The reaction was stirred under hydrogen atmosphere (30 psi). The reaction was monitored by TLC. It was then filtered through sintered funnel with a pad of celite, washed with methanol and concentrated under reduced pressure to afford precursor-05 as a brown colored gummy solid (4.0 g, 99percent yield) that was used as such for the next step without any further purification. ‘H NMR (400 MHz, CDC13): 6 7.12 (s, 1H), 6.97 (s, IH), 3.78 (s, 3H), 2.87 (br s, 2H).
92% With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 18 h; Under hydrogen (1 atm), to a solution of compound 15-b (1.0 g, 7.87 mmol) in ethanol (15 mL) was added 10percent Pd—C (0.2 g). The mixture was stirred at 25° C. for 18 hours, and then filtrated, the filtrate was concentrated under reduced pressure, the residue was purified by silica column chromatography (petroleum ether:ethyl acetate=1:1) to give red oil 15-a (700 mg, yield: 92percent).
83.7% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Inert atmosphere Pd / C (10percent, 500 mg) was added to the column1-methyl-4-nitro-1H-pyrazole (1.90 g, 14.9 mmol)And methanol (25 mL)Hydrogen at room temperature overnight.Diatomaceous earth filter, dichloromethane washing filter cake,The filtrate was concentrated under reduced pressure, (Eluent: ethyl acetate / methanol (v / v) = 18/1) to give 1.35 g of a black solid, yield:83.7percent.
80% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 6 h; Step 1: 1-Methyl-1H-pyrazol-4-amine[2226]To 10 mL of methanol were added 1-methyl-4-nitro-1H-pyrazole (500 mg, 3.93 mmol) and Pd/C (10, 50 mg) . The mixture was stirred at rt for 6 hours under hydrogen atomosphere at ordinary pressure, then filtered. The filtrate was concentrated to give red liquid (305 mg, 80) .[2227]1H NMR (600 MHz, CDCl3) : δ ppm 7.18 (s, 1H) , 7.14 (s, 1H) , 3.78 (s, 3H) and MS-ESI: m/z 98.20 [M+H]+.
73% With hydrogen In ethanol; ethyl acetate at 20℃; for 14 h; Example 25Synthesis of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amineThe compound was synthesized according to Method A.A mixture of 0.996 g (8.82 mmol) of 4-nitropyrazole (J. Med. Chem. 2005, 48, 5780-5793) and 1.33 g (10.6 mmol) of dimethyl sulphate in 10 mL of 1 M NaOH was heated at 35° C. for 48 hrs. The reaction mixture was cooled to RT and the precipitate was filtered, washed with water, and dried to give 0.561 g (50percent yield) of 1-methyl-4-nitro-1H-pyrazole: 1H NMR (DMSO-d6) δ8.83 (s, 1H), 8.22 (s, 1H), 3.91 (s, 3H).A mixture of 0.144 g (1.14 mmol) 1-methyl-4-nitro-1H-pyrazole, 0.017 g (0.07 mmol) platinum oxide, and ethyl acetate (5 mL) in ethanol (15 mL) was stirred under 2 atmospheres of hydrogen for 14 hrs. The catalyst was removed by filtration through a pad of celite and the solvent was removed to give 0.080 mg (73percent yield) of 4-amino-1-methyl-1H-pyrazole as a purple residue, which was used in the next step without further purification: 1H NMR (DMSO-d6) δ6.98 (s, 1H), 6.88 (s, 1H), 3.76 (br s, 2H), 3.65 (s, 3H).A mixture of 0.405 g (4.27 mmol) of 4-amino-1-methylpyrazole and 0.695 g (1.90 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-1H-benzimidazole in DMSO (5 mL) was heated at 125° C. for 15 min. The reaction mixture was cooled to room temperature and water was added. The solid was collected by filtration, washed with water, and dried. Chromatography on alumina, eluting with hexanes/EtOAc (1:1) gave a brown powder. Recrystallization from ethanol/CH2Cl2 gave 0.145 g (18percent yield) of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-N-(1-methyl-1H-pyrazol-4-yl)-6-(4-morpholinyl)-1,3,5-triazin-2-amine: mp 225-226° C.; 1H NMR (DMSO-d6) (rotamers) δ10.00 (s, 1H), 9.73 (s, 0.2H), 8.60 (d, J=8.0 Hz, 1H), 8.29 (d, J=7.6 Hz, 0.2H), 7.92 (t, JHF=52.8 Hz, 1H), 7.86-7.80 (m, 2.6H), 7.68 (t, JHF=52.6 Hz, 0.2H), 7.59 (s, 1H), 7.52-7.42 (m, 2.9H), 3.85-3.82 (m, 8.4H), 3.75-3.73 (m, 4.8H); Anal. Calcd. for C19H19F2N9O 0.06EtOAc 0.24H2O: C, 52.9; H, 4.6; N, 28.8. Found: C, 52.9; H, 4.5; N, 28.6percent.

Reference: [1] Patent: US2011/251176, 2011, A1, . Location in patent: Page/Page column 160-161
[2] Patent: WO2015/25197, 2015, A1, . Location in patent: Paragraph 00077
[3] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0179; 0181
[4] Patent: CN106432246, 2017, A, . Location in patent: Paragraph 0453; 0806; 0807; 0808
[5] Patent: WO2015/161830, 2015, A1, . Location in patent: Paragraph 00770
[6] Patent: US2011/9405, 2011, A1, . Location in patent: Page/Page column 49
[7] Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 997 - 1000
[8] Patent: US5252538, 1993, A,
[9] Patent: WO2006/40520, 2006, A1, . Location in patent: Page/Page column 123
[10] Patent: WO2007/99326, 2007, A1, . Location in patent: Page/Page column 109-110
[11] Patent: WO2007/99317, 2007, A1, . Location in patent: Page/Page column 113
[12] Patent: WO2007/99335, 2007, A1, . Location in patent: Page/Page column 101
[13] Patent: US2009/76075, 2009, A1, . Location in patent: Page/Page column 42
[14] Patent: WO2012/62704, 2012, A1, . Location in patent: Page/Page column 48
[15] Patent: WO2014/20531, 2014, A1, . Location in patent: Page/Page column 38-39
[16] Journal of the American Chemical Society, 2014, vol. 136, # 34, p. 11878 - 11881
[17] Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 10013 - 10030
[18] Patent: CN106986860, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032
[19] Patent: CN107098861, 2017, A, . Location in patent: Paragraph 0032; 0034
[20] Chemical Biology and Drug Design, 2018, vol. 91, # 2, p. 567 - 574
[21] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2382 - 2390
[22] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0133-0134
[23] Patent: WO2007/113548, 2007, A1, . Location in patent: Page/Page column 158
[24] Patent: WO2007/113565, 2007, A1, . Location in patent: Page/Page column 101
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Reference: [1] Patent: WO2010/10184, 2010, A1, . Location in patent: Page/Page column 60
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  • [ 2075-46-9 ]
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Reference: [1] Patent: WO2011/134831, 2011, A1, . Location in patent: Page/Page column 36
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Reference: [1] Patent: WO2013/17479, 2013, A1, . Location in patent: Page/Page column 45
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  • [ 127107-23-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1989, p. 1941 - 1946
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