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[ CAS No. 304897-49-2 ] {[proInfo.proName]}

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Chemical Structure| 304897-49-2
Chemical Structure| 304897-49-2
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Product Details of [ 304897-49-2 ]

CAS No. :304897-49-2 MDL No. :MFCD06797795
Formula : C16H25N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZTYRRWNDQSVOCL-UHFFFAOYSA-N
M.W : 291.39 Pubchem ID :12045001
Synonyms :

Calculated chemistry of [ 304897-49-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 92.3
TPSA : 58.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.08
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : 1.62
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.62
Solubility : 0.692 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (Ali) : -2.59
Solubility : 0.746 mg/ml ; 0.00256 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.12
Solubility : 0.223 mg/ml ; 0.000764 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.27

Safety of [ 304897-49-2 ]

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 [ 304897-49-2 ]

* 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 [ 304897-49-2 ]
  • Downstream synthetic route of [ 304897-49-2 ]

[ 304897-49-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 130636-61-2 ]
  • [ 304897-49-2 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen In ethyl acetate for 2 h; Example 2
Synthesis of Compound 5
tert-Butyl 4-[4-(cis-4,7,10,13,16,19-docosahexenoyl)amino]benzyl-1-piperazinecarboxylate (5).
To compound 3 (0.68 g, 2.1 mmol) in ethyl acetate (100 mL) was added 10percent Pd/C (0.1 g), and the reaction mixture was hydrogenated for 2 h under a pressure of 60 lb/inch2.
The product was filtered, and solvent was removed in vacuo to afford amine 4 (0.6 g, 97percent yield).
Without further purification, to amine 4 (0.6 g, 2.06 mmol) dissolved in acetonitrile (90 mL) was added cis-4,7,10,13,16,19-docosahexenoic acid (DHA, 0.67 g, 2.0 mmol), 2-(1-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU, 0.94 g, 2.5 mmol), and N,N-diisopropylethylamine (2.1 mL).
The reaction mixture was stirred overnight.
Solvent was removed in vacuo, and the product was purified by column chromatography, eluding with ethyl acetate to afford 5 as an oil (0.91 g, 73percent yield).
1H NMR (DMSO-d6): 9.84 (s, 1H, NH), 7.53-7.51 (d, 2H, J=8.80 Hz, Ar-H), 7.19-7.17 (d, 2H, J=8.40 Hz, Ar-H), 5.35-5.31 (m, 12H, CH=CH), 3.40 (s, 2H, CH2), 3.29 (brs, 4H, 2*CH2), 2.83-2.75 (m, 10H, 5*CH2), 2.35 (brs, 4H, 2*CH2), 2.27 (t, 4H, J=4.80 Hz, 2*CH2), 2.04-2.00 (m, 2H, CH2), 1.38 (s, 9H, 3*CH3), 0.91 (t, 3H, J=7.20 Hz, CH3). Anal. (C38H55N3O3.4.1H2O) C, H, N
90.2% With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 12 h; A solution of tert-butyl 4-(4-nitrobenzyl)piperazine-1-carboxylate (1.100 g, 3.423 mmol), ammonium chloride (0.915 g, 17.114 mmol) and Zn dust (1.119 g, 17.114 mmol) in tetrahydrofuran (20 mL) / water (20 mL) was stirred at the room temperature for 12 hr. The reaction mixture was filtered to remove solids. Then, water was added to the filtrate, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous Mg504, filtered, and concentrated in vacuo. The title compound was used without further purification (tert-butyl 4-(4-aminobenzyl)piperazine-1-carboxylate, 0.900 g, 90.2 percent, yellow solid).
81% With tin(II) chloride dihdyrate In ethyl acetate at 20℃; To a solution of tert-butyl 4-(4-nitrobenzyl)piperazine-1-carboxylate derivatives (1 mmol) (compound (ST) with suitable substitution) in ethyl acetate (O.12M ml), tin(ii) chloride dihydrate (5 mmol) was added and the resulting mixture was left stirring at RT overnight.Then, saturated aqueous solution of sodium bicarbonate (20 mL) was addedand vigorously stirred for 1 hour. Solids were removed by filtration throught a celite pad and the organic layer of the filtrate was separated and washed with water (20 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated to give the following compounds of Formula (X).
72% With hydrogen In ethyl acetate for 2 h; ferf-Butyt 4-(4-nitrobenzyl)piperazine-1-carboxylate (I92) (0.500 g, 1.56 mmol), ethyl acetate (100 mL) and 10percent Pd/C (150 mg) were agitated under a hydrogen atmosphere at 50 psi. After two hours the mixture was filtered through celite and concentrated. The residue was chromatographed (12 g silica cartridge, 0-60percent ethyl acetate/petroleum benzine 40-60 °C) to give the title compound (193) (327 mg, 72percent yield) as a white solid; 1H N R (400 MHz, CDCI3) δ 7.11 - 7.05 (m, 2H), 6.67 - 6.61 (m, 2H), 3.62 (s, 2H), 3.43 - 3.37 (m, 6H), 2.40 - 2.30 (m, 4H), 1.45 (s, 9H). LCMS Method C: rt 1.80 min; m/z 292.1 [M+H]+
72% With palladium 10% on activated carbon; hydrogen In ethyl acetate for 2 h; terf-Butyl 4-(4-nitrobenzyl)piperazine-1-carboxylate (192) (0.500 g, 1.58 mmol), ethyl acetate (100 mL) and 10percent Pd/C (150 mg) were agitated under a hydrogen atmosphere at 50 psi. After two hours the mixture was filtered through celite and concentrated. The residue was chromatographed (12 g silica cartridge, 0-60percent ethyl acetate/petroleum benzine 40-60 °C) to give the title compound {193) (327 mg, 72percent yield) as a white solid; 1H N R (400 Hz, CDCI3) δ 7.11 - 7.05 (m, 2H), 6.67 - 6.61 (m, 2H), 3.62 (s, 2H), 3.43 - 3.37 (m, 6H), 2.40 - 2.30 (m, 4H), 1.45 (s, 9H). LCMS Method C: rt 1.80 min; m/z 292.1 [M+H]+.
67% at 30℃; A solution of 4-(4-nitro-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (2.82 g, 8.77 mmol) was hydrogenated on an H-Cube apparatus with a 5percent Pd/C cartridge under the following conditions: flow rate=1 mL/min, heating column temperature=30° C., H2 pressure=40 bar. The material was passed through the column twice more in order to complete the reaction. Solvents were evaporated in vacuo. Purification of the residue on a 50-g Isolute SPE column on a FlashMaster system with 25-50percent EtOAc-hexane afforded the title compound (1.70 g, 67percent) as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C16H25N3O2, 292.2 (M+H), found 292.1.

Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 19, p. 5592 - 5599
[2] Patent: US2004/34033, 2004, A1, . Location in patent: Page/Page column 12; Sheet 1
[3] Patent: WO2017/18803, 2017, A1, . Location in patent: Paragraph 1492; 1493; 1494
[4] Patent: WO2016/146220, 2016, A1, . Location in patent: Page/Page column 26; 27
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1499 - 1518
[6] Patent: WO2012/110773, 2012, A1, . Location in patent: Page/Page column 120; 121
[7] Patent: WO2014/27199, 2014, A1, . Location in patent: Page/Page column 123
[8] Patent: US2007/249649, 2007, A1, . Location in patent: Page/Page column 116
[9] Archiv der Pharmazie, 2000, vol. 333, # 8, p. 267 - 274
[10] Patent: US2003/69299, 2003, A1,
[11] Patent: US2007/167435, 2007, A1, . Location in patent: Page/Page column 47
  • 2
  • [ 100-11-8 ]
  • [ 304897-49-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 19, p. 5592 - 5599
[2] Patent: WO2012/110773, 2012, A1,
[3] Patent: WO2014/27199, 2014, A1,
[4] Patent: WO2016/146220, 2016, A1,
[5] Patent: WO2017/18803, 2017, A1,
[6] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1499 - 1518
  • 3
  • [ 57260-71-6 ]
  • [ 304897-49-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 19, p. 5592 - 5599
[2] Patent: WO2012/110773, 2012, A1,
[3] Patent: WO2014/27199, 2014, A1,
[4] Patent: WO2016/146220, 2016, A1,
[5] Patent: WO2017/18803, 2017, A1,
[6] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1499 - 1518
  • 4
  • [ 58198-49-5 ]
  • [ 304897-49-2 ]
Reference: [1] Archiv der Pharmazie, 2000, vol. 333, # 8, p. 267 - 274
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