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[ CAS No. 1029413-55-5 ] {[proInfo.proName]}

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Chemical Structure| 1029413-55-5
Chemical Structure| 1029413-55-5
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Product Details of [ 1029413-55-5 ]

CAS No. :1029413-55-5 MDL No. :MFCD10687120
Formula : C13H22N4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :TVJWTRPGFVNAJI-UHFFFAOYSA-N
M.W : 266.34 Pubchem ID :27281520
Synonyms :

Calculated chemistry of [ 1029413-55-5 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.69
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 77.57
TPSA : 73.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 0.89
Log Po/w (WLOGP) : 1.66
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : -0.02
Consensus Log Po/w : 1.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.98
Solubility : 2.77 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (Ali) : -2.02
Solubility : 2.57 mg/ml ; 0.00964 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.45
Solubility : 9.54 mg/ml ; 0.0358 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.58

Safety of [ 1029413-55-5 ]

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 [ 1029413-55-5 ]

* 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 [ 1029413-55-5 ]
  • Downstream synthetic route of [ 1029413-55-5 ]

[ 1029413-55-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1201916-87-1 ]
  • [ 1029413-55-5 ]
YieldReaction ConditionsOperation in experiment
78.7% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2 h; Step 3) fert-butyl 4-(4-amino-lH-pyrazol-l-yl)piperidine-l-carboxylate [0409] To a solution of tert-butyl 4-(4-nitro-lH-pyrazol-l-yl)piperidine-l-carboxylate (1.35 g, 4.56 mmol) in ethanol (30 mL) was added Pd/C (135 mg, 1.269 mmol, mass percent = 10percent). The mixture was stirred under a H2 atmosphere at rt for 2 h .The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 50/1 to 25/1) to give the title product as brown oil (955 mg, yield 78.7percent). LC-MS (ESI, pos. ion) m/z: 211.1 [M-55] +.
78.7% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2 h; To a solution of tert-butyl 4-(4-nitro-IH-pyrazol-1-yl)piperidine-1-carboxylate (1.35 g,4.56 mmol) in ethanol (30 mL) was added Pd/C (135 mg, 1.269 mmol, mass percent = 10percent). Themixture was stirred at rt under a H2 atmosphere for 2 h .The resulting mixture was filtered andthe filtrate was concentrated in vacuo. The residue was purified by silica gel columnchromatography (DCM/MeOH (v/v) = 50/1 to 25/1) to give the title product as brown oil (955mg, yield 78.7percent).LC-MS (ESI, pos. ion) m/z: 211.1 [M-55] +.
78.7% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; To a solution of tert-butyl 4- (4-nitro-1H-pyrazol-1-yl) piperidine-1-carboxylate (1.35 g, 4.56 mmol) in ethanol (30 mL) was addedPd / C(135 mg, 10percent content).The reaction system was incubated at room temperature,Reaction in a hydrogen atmosphere for 2 hours,then,The reaction mixture was filtered,The filtrate was concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 50/1 to 25/1)The title compound was obtained as a yellow solid (955 mg, yield 78.7percent).
78.7% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2 h; To a solution of tert-butyl 4- (4-nitro-1H-pyrazol-1-yl) piperidine-1-carboxylate (1.35 g, 4.56 mmol) in ethanol(30 mL) was added Pd / C (135 mg, 10percent by mass). The reaction system was allowed to react at room temperature for 2 hours in a hydrogen atmosphere, The reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was chromatographed on silica gel (DCM / MeOH (v / v) = 50/125/1) to give the title compound as a brown oil (955 mg, yield 78.7percent).
72% With palladium 10% on activated carbon; hydrogen In ethanol for 24 h; Added 10percent palladium on carbon (130 mg) to a solution of B5 (1 .31 g, 4.422) in ethanol (60 mL) and left under an atmosphere of hydrogen for 24 h. Filtered the reaction mixture through Celite washing with ethyl acetate and remove the solvent from the filtrate. Purified by flash chromatography using methanol/chloroform (4/96) to give the titled compound JAR-506-019- 01 (843 mg, 72percent). LCMS (Method 1 ) Rt 1 .907 min, ESIMS m/z [M+H]+ 267.3.
70% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; Inert atmosphere To a stirred solution of tert-butyl 4-(4-nitro-IH-pyrazol-1-yl)piperidine-1-carboxylate (2.5 g,6.7 mmol) in dry MeOH (30 mL), was added 10percent palladium on charcoal (250 mg) under nitrogen atmosphere. The reaction was stirred at rt for 3 h under hydrogen atmosphere. The reaction progress was monitored by TLC. After completion of reaction, the reaction mixture was filtered through celite and washed with MeOH. The filtrate was concentrated toget the title compound. Yield: 70percent (2 g, brown solid). 1H NMR (400 MHz, DMSO-d6): 67.06 (5, IH), 6.91 (5, IH), 4.16-4.08 (m, IH), 4.01-3.98 (m, 2H), 3.77 (brs, 2H), 3.21-2.87(m, 2H), 1.92-1.89 (m, 2H), 1.72-1.41 (m, 2H), 1.40 (5, 9H). LCMS: (Method A) 267.3 (M+H), Rt. 1.98 mm, 93.97 percent (Max).
70% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; To a stirred solution of tert-butyl 4-(4-nitro-1 H-pyrazol-1-yl)piperidine-1-carboxylate (2.5 g, 6.7 mmol) in dry MeOH (30 mL), was added 10percent palladium on charcoal (250 mg) under nitrogen atmosphere. The reaction was stirred at rt for 3 h under hydrogen atmosphere. The reaction progress was monitored by TLC. After completion of reaction, the reaction mixture was filtered through celite and washed with MeOH. The filtrate was concentrated to get the title compound. Yield: 70percent (2 g, brown solid). 1H NMR (400 MHz, DMSO-d6): δ 7.06 (s, 1 H), 6.91 (s, 1 H), 4.16-4.08 (m, 1 H), 4.01-3.98 (m, 2H), 3.77 (br s, 2H), 3.21 -2.87 (m, 2H), 1.92-1.89 (m, 2H), 1.72-1.41 (m, 2H), 1.40 (s, 9H). LCMS: (Method A) 267.3 (M +H), Rt. 1.98 min, 93.97 percent (Max).
64% With hydrogen In ethanol at 17 - 25℃; for 18 h; Inert atmosphere b) A mixture of tert-butyl 4-(4-nitropyrazol- 1 -yl)piperidine- 1 -carboxylate (3.63 g, 12.25 mmol) and 10percent palladium on carbon (0.326 g, 0.31 mmol) in EtOH (200 mL) were stirred under an atmosphere of hydrogen for 18 hours. The mixture was filtered through Celite and the filtrate loaded onto an SCX column. The mixture was eluted first with MeOH and then with a 7M solution OfNH3 in MeOH. Fractions containing product were combined and evaporated to afford tert-butyl 4-(4-aminopyrazol-l-yl)piperidine-l- carboxylate (2.100 g, 64percent yield); 1H NMR spectrum: (300 MHz, DMSO) δ 1.41 (9H, s), 1.65 - 1.74 (2H, m), 1.89 - 1.92 (2H, m), 2.81 - 2.93 (2H, m), 3.75 (2H, s), 3.99 (2H, d), 4.09 - 4.16 (IH, m), 6.91 (IH, s), 7.06 (IH, s); Mass spectrum: m/z (ESI+) (M+H)+ = 211.0.
1.1 g With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; Palladium on carbon (10percent w/w, 0.2 g) is added to a solution of tert-butyl 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylate (2.1 g, 0.0040 mol) in methanol (50 ml), and the mixture is hydrogenated at room temperature for 3 h. The catalyst is filtered off, and the solution is evaporated in a rotary evaporator. The residue is purified by chromatography, giving 1.1 g of a brown oil; [0558] 1H NMR (400 MHz, DMSO-d6): 8 [ppm] 7.05 (d, J=0.8 Hz, 1H), 6.89 (d, J=0.8 Hz, 1H), 4.14 (m, 1H), 3.99 (d, 2H), 3.84 (d, 2H), 2.84 (bs, 2H), 1.90-1.87 (m, 2H), 1.70-1.61 (m, 2H), 1.40 (s, 9H);

Reference: [1] Patent: WO2017/44434, 2017, A1, . Location in patent: Paragraph 0409
[2] Patent: WO2017/48675, 2017, A1, . Location in patent: Paragraph 0456
[3] Patent: CN106478651, 2017, A, . Location in patent: Paragraph 1004; 1005; 1006
[4] Patent: CN106478607, 2017, A, . Location in patent: Paragraph 0673; 0674; 0675
[5] Patent: WO2015/123722, 2015, A1, . Location in patent: Page/Page column 90
[6] Patent: WO2017/144633, 2017, A1, . Location in patent: Page/Page column 106
[7] Patent: WO2017/144639, 2017, A1, . Location in patent: Page/Page column 91
[8] Patent: WO2009/153589, 2009, A1, . Location in patent: Page/Page column 129
[9] Tetrahedron Letters, 2008, vol. 49, # 18, p. 2996 - 2998
[10] Patent: US2014/228340, 2014, A1, . Location in patent: Paragraph 0556-0559
[11] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4859 - 4866
[12] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0411-0412
  • 2
  • [ 109384-19-2 ]
  • [ 1029413-55-5 ]
Reference: [1] Patent: US2010/317680, 2010, A1,
[2] Patent: US2014/228340, 2014, A1,
[3] Patent: WO2015/123722, 2015, A1,
[4] Patent: WO2017/48675, 2017, A1,
[5] Patent: CN106478651, 2017, A,
[6] Patent: WO2017/44434, 2017, A1,
[7] Patent: CN106478607, 2017, A,
[8] Patent: WO2017/144633, 2017, A1,
[9] Patent: WO2017/144639, 2017, A1,
[10] Patent: US2018/208604, 2018, A1,
[11] Patent: WO2009/153589, 2009, A1,
  • 3
  • [ 2075-46-9 ]
  • [ 109384-19-2 ]
  • [ 1029413-55-5 ]
Reference: [1] Patent: WO2014/26242, 2014, A1, . Location in patent: Page/Page column 164
  • 4
  • [ 5382-16-1 ]
  • [ 1029413-55-5 ]
Reference: [1] Patent: WO2017/48675, 2017, A1,
[2] Patent: CN106478651, 2017, A,
[3] Patent: WO2017/44434, 2017, A1,
[4] Patent: CN106478607, 2017, A,
  • 5
  • [ 141699-59-4 ]
  • [ 1029413-55-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4859 - 4866
[2] Patent: WO2017/144633, 2017, A1,
[3] Patent: WO2017/144639, 2017, A1,
  • 6
  • [ 24424-99-5 ]
  • [ 1029413-55-5 ]
Reference: [1] Patent: WO2017/48675, 2017, A1,
[2] Patent: WO2017/44434, 2017, A1,
  • 7
  • [ 34619-03-9 ]
  • [ 1029413-55-5 ]
Reference: [1] Patent: CN106478651, 2017, A,
[2] Patent: CN106478607, 2017, A,
  • 8
  • [ 79099-07-3 ]
  • [ 1029413-55-5 ]
Reference: [1] Patent: WO2014/26242, 2014, A1,
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