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[ CAS No. 509073-62-5 ] {[proInfo.proName]}

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Chemical Structure| 509073-62-5
Chemical Structure| 509073-62-5
Structure of 509073-62-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 509073-62-5 ]

CAS No. :509073-62-5 MDL No. :MFCD06659593
Formula : C16H21N3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :XHGPWZQBCGONPX-UHFFFAOYSA-N
M.W : 335.36 Pubchem ID :2764459
Synonyms :

Calculated chemistry of [ 509073-62-5 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 97.13
TPSA : 95.67 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.92
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 1.01
Log Po/w (SILICOS-IT) : -0.54
Consensus Log Po/w : 1.36

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.436 mg/ml ; 0.0013 mol/l
Class : Soluble
Log S (Ali) : -3.5
Solubility : 0.106 mg/ml ; 0.000316 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.38
Solubility : 1.4 mg/ml ; 0.00419 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.52

Safety of [ 509073-62-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 509073-62-5 ]

* 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 [ 509073-62-5 ]
  • Downstream synthetic route of [ 509073-62-5 ]

[ 509073-62-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 509073-62-5 ]
  • [ 350684-49-0 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 18 h; [0260j A mixture of tert-butyl 4-(4-nitrobenzoyl)piperazine- 1 -carboxylate (20 g, 60 mmol) and 10percent Pd/C (4 g) in MeOH (600 mL) was stirred under 1 atmosphere of H2 at room temperature for for 18 h. The solution was filtered through Celite and the filtrate was concentrated under reduced pressure to afford 18 g of tert-butyl 4-(4- aminobenzoyl)piperazine-1-carboxylate as a white solid (100percent).
98% With palladium 10% on activated carbon; hydrogen In methanol for 12 h; A solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (4) (335 mg, 1 mmol) in 30 mL of anhydrous methanol wasadded 10percent Pd / percent (W / w), 34 mg) hydrogenation catalyst. Vacuum, pour hydrogen, stir the reaction overnight. 12After theaddition of Pd / C, the solvent was removed by evaporation under reduced pressure to give a white solid which was subjectedto the next reaction without purification.
98% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; To a degassed solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (2c, 4.1 g, 12.3 mmol, 1 equiv.) in anhydrous MeOH (40 mL) was added Pd/C (10percent wt., dry; 600 mg).The reaction was sealed, fifted with a H2 balloon and then stirred for 3 h at room temperature. The reaction mixture was filtered through Celite and then concentrated to obtain the product 2d as a white foam (3.7 g, 12 mmol, 98percent yield).
98% With palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 3 h; Sealed tube To a degassed solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (2c, 4.1 g, 12.3 mmol, 1 equiv.) in anhydrous MeOH (40 mL) was added Pd/C (10percent wt., dry; 600 mg). The reaction was sealed, fitted with a H2 balloon and then stirred for 3 h at room temperature. The reaction mixture was filtered through Celite and then concentrated to obtain the product 2d as a white foam (3.7 g, 12 mmol, 98percent yield).
93% With hydrogen In methanol at 20℃; Step b - terf-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate; <n="163"/>A solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (1.0Og, 3.00mmol) in MeOH (60ml) was hydrogenated at 2O0C at atmospheric pressure using an H-Cube (flow rate at 1 ml/min and full hydrogen mode) using a Pd/C cartridge. The solvent was removed in vacuo Xo afford te/f-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate (0.85g, 2.79mmol, 93percent) as a white solid. 1H NMR (CDCI3) δ 1.41 (9H, s), 3.38 (4H, m), 3.53 (4H, m), 4.07 (2H, br. s), 6.55 (2H, d), 7.17 (2H, d). LCMS (2) Rt: 2.14min; m/z (ES+) 306.

Reference: [1] Patent: WO2013/177536, 2013, A2, . Location in patent: Paragraph 0260
[2] Patent: CN102464631, 2016, B, . Location in patent: Paragraph 0094-0096
[3] Patent: WO2018/98275, 2018, A1, . Location in patent: Page/Page column 126
[4] Patent: WO2018/98288, 2018, A1, . Location in patent: Page/Page column 154; 155
[5] Patent: WO2008/139161, 2008, A1, . Location in patent: Page/Page column 161-162
[6] Patent: WO2010/80474, 2010, A1, . Location in patent: Page/Page column 141
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