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Chemical Structure| 54535-22-7
Chemical Structure| 54535-22-7
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Product Details of [ 54535-22-7 ]

CAS No. :54535-22-7 MDL No. :MFCD00173404
Formula : C14H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :PYPCDUKQEIPHAF-UHFFFAOYSA-N
M.W : 263.29 Pubchem ID :264327
Synonyms :

Calculated chemistry of [ 54535-22-7 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 8
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 71.49
TPSA : 64.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.04
Log Po/w (XLOGP3) : 3.25
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 1.74
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.157 mg/ml ; 0.000595 mol/l
Class : Soluble
Log S (Ali) : -4.28
Solubility : 0.0138 mg/ml ; 0.0000524 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.5
Solubility : 0.0825 mg/ml ; 0.000313 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.55

Safety of [ 54535-22-7 ]

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 [ 54535-22-7 ]

* 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 [ 54535-22-7 ]
  • Downstream synthetic route of [ 54535-22-7 ]

[ 54535-22-7 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 54535-22-7 ]
  • [ 34785-11-0 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 344, p. 163 - 168
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1264
[3] Patent: US2011/98311, 2011, A1,
  • 2
  • [ 54535-22-7 ]
  • [ 26892-90-0 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 70℃; for 4 h;
Stage #2: With sodium carbonate In water
4-Hydroxyquinoline-3-carboxylic acid ethyl ester
A 1 L three-necked flask fitted with a mechanical stirrer was charged with 2-phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g).
The mixture was heated to 70° C. and stirred for 4 h.
The mixture was cooled to room temperature and filtered.
The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried.
4-Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70percent).
70%
Stage #1: at 70℃; for 4 h;
Stage #2: With sodium carbonate In water at 20℃;
[0217] A l L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 0C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4-Hydroxyquinoline-3- carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70percent). The crude product was used in next step without further purification.
65% at 75℃; for 8 h; General procedure: Polyphosphoric acid (PPA) (2 equiv by weight) was added to corresponding intermediate 1 (40 mmol) to this phosphorousoxychloride (POCl3) (10 mmol) was added. The reaction mixture was heated to 75 °C for 8 h, monitored by TLC, after completion of the reaction. The reaction mixture was quenched slowly with 10percent sodium hydroxide solution by keeping it in an ice bath and the PH was adjusted to a pH ~ 7, the solid separated was filtered, dried and washed with diethyl ether (3*20 mL) to afford desired compound in good yield. 4.1.5.1. Ethyl 4-hydroxyquinoline-3-carboxylate (10a). Pale yellowsolid (5.64 g, 65percent); m.p: 276-278 C; ESI-MS was found at m/z 218.32 [M+H]+. 1H NMR (300 MHz, DMSO-d6, TMS):d 10.72 (brs,1H), 8.91 (s, 1H), 8.46e7.78 (m, 4H), 4.29 (q, J 7.1 Hz, 2H), 1.29 (t,J 7.1 Hz, 3H).
Reference: [1] Patent: US4079058, 1978, A,
[2] Patent: US2008/90864, 2008, A1, . Location in patent: Page/Page column 7
[3] Patent: WO2007/79139, 2007, A2, . Location in patent: Page/Page column 46
[4] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 1 - 16
[5] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 344, p. 163 - 168
[6] Journal of the American Chemical Society, 1939, vol. 61, p. 2890,2893
[7] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 2980 - 2985
[8] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6351 - 6363
[9] Patent: US2008/306048, 2008, A1, . Location in patent: Page/Page column 17
[10] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 1948 - 1956
[11] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 689 - 693
[12] Patent: US2012/309758, 2012, A1, . Location in patent: Page/Page column 60
[13] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 0351
[14] Patent: WO2018/64632, 2018, A1, . Location in patent: Paragraph 00213; 00214
[15] Patent: WO2018/107100, 2018, A1, . Location in patent: Paragraph 00232; 00233
[16] Patent: US2018/280349, 2018, A1, . Location in patent: Paragraph 0096
  • 3
  • [ 54535-22-7 ]
  • [ 497-19-8 ]
  • [ 26892-90-0 ]
Reference: [1] Patent: US2011/98311, 2011, A1,
  • 4
  • [ 101-84-8 ]
  • [ 92-52-4 ]
  • [ 54535-22-7 ]
  • [ 26892-90-0 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1264
  • 5
  • [ 54535-22-7 ]
  • [ 13720-94-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 21, p. 6351 - 6363
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1448 - 1452
[3] ChemBioChem, 2014, vol. 15, # 9, p. 1280 - 1285
[4] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 1 - 16
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1205 - 1210
  • 6
  • [ 54535-22-7 ]
  • [ 13721-01-2 ]
Reference: [1] Chemical Communications, 2005, # 43, p. 5438 - 5440
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6443 - 6450
[3] Patent: US2011/230519, 2011, A1,
[4] Patent: US2012/309758, 2012, A1,
[5] Patent: WO2013/67410, 2013, A1,
[6] Patent: WO2014/71122, 2014, A1,
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5405 - 5418
[8] Patent: WO2014/118805, 2014, A1,
[9] Patent: WO2015/73231, 2015, A1,
[10] Patent: US2015/231142, 2015, A1,
[11] Patent: WO2015/189560, 2015, A1,
[12] Medicinal Chemistry Research, 2016, vol. 25, # 9, p. 1861 - 1876
[13] Patent: WO2007/79139, 2007, A2,
[14] Patent: US2011/98311, 2011, A1,
[15] Patent: WO2018/64632, 2018, A1,
[16] Patent: WO2018/107100, 2018, A1,
[17] Patent: US2018/280349, 2018, A1,
[18] Patent: US2017/96397, 2017, A1,
[19] Patent: WO2018/227049, 2018, A1,
  • 7
  • [ 62-53-3 ]
  • [ 87-13-8 ]
  • [ 54535-22-7 ]
YieldReaction ConditionsOperation in experiment
100% at 120 - 130℃; for 16.5 h; Aniline (2.733 mL, 29.99 mMol) was stirred in diethyl ethoxymethylenemalonate (6.063 mL, 30.00 mMol) at 120-130°C for 16.5 hours. T.l.c. analysis (ethyl acetate cyclohexane, 1 : 1) showed the presence of one UV-active product (Rf 0.84) and complete consumption of both starting materials. Upon cooling down of the reactionsolution to room temperature, intermediate diethyl 2-((phenylamino)methylene)malonate 35 solidified (as dark yellow crystalline solid,7.899 g, quant.). M.p. 36-37°C; HRMS (EIj: found 263.11531 [M] C14H17N04requires 263.11521; Vmax (thin film): 3265, 3184 (w, NH), 3050 (w, ArC-H), 2981,2936, 2904, 2871 (m, alkyl C-H), 1717 (s, 2 x intramolecularly hydrogen-bondedC=O conjugated with C=C), 1691 (s, C=C-NH), 1655 (s, C=N-), 1623 (s, aryl conjugated C=C), 1255 (s, C-N stretch) cm’; 6H (CD3CN, 500 MHz): 1.31 (3H, t, JCH3,CH2 7.1 Hz, CH3), 1.32 (3H, t, JCH3,CH2 7.2 Hz, CH3), 4.19 (2H, q, JCH2,CH3 7.2 Hz, CH2), 4.25 (2H, q, JCH2,CH3 7.1 Hz, CH2), 7.16 (1H, tt, JparaArH,metaArHs 7.4 Hz, JparaArH,orthoArHs 1.1 Hz, para-ArH), 7.20 (2H, dt, Jortho&-Hs,metaArHs 7.6 Hz,JorthoArHsparaArH 1.0 Hz, 2 x orthoArHs), 7.38 (2H, m, J 7.4 Hz, 2 x metaArHs), 8.48(1H, d, JCH,NH 13.8 Hz, CH-NH), 10.81 (1H, d, JNH,CH 13.6 Hz, CH-NI]); 6c(CD3CN, 125 MHz): 14.1, 14.2 (2 x CH3), 60.3, 60.6(2 x CH2), 93.9 (O=C-C-C=O),117.6(2 x orthoArCs), 125.1 (paraArC), 130.1 (2 x metaArCs), 139.8 (ArCquat-NH),151.9 (NH-CH), 165.6 (C=O), 168.8 (hydrogen bonded C=O).
90% Reflux General procedure: To a stirred solution of substituted aniline 8 (50 mmol), diethyl 2-(ethoxymethylene)malonate (55 mmol) in ethanol (EtOH) (250 mL) was refluxed for 3 h. TLC analysis indicated that the reaction was complete. After cooling the reaction mixture solid was separated. The separated solid was filtered and washed with 3percent ethyl acetate:hexane for further purification to afford desired compound as an off-white solid in good yield (89-92percent). 4.1.4.1. Diethyl 2-((phenylamino)methylene)malonate (9a). The compound was prepared according to the general procedure C using compound 8a (4.65 g, 50 mmol), diethyl 2-(ethoxymethylene)malonate (11.87 g, 55 mmol) as an off-white solid (11.83 g, 90percent); m.p: 94-96 C; ESI-MS was found at m/z 264.23 [M+H]+. 1H NMR (300 MHz, CDCl3, TMS):d 8.46 (s, 1H), 7.32e6.84(m, 5H), 6.62 (s, 1H), 4.35 (q,J 7.0 Hz, 4H), 1.32 (t,J 6.8 Hz, 6H).
82% for 3 h; Reflux General procedure: A solution of the appropriate aniline (100 mmol), and diethyl ethoxymethylenemalonate (20.4 mL,100 mmol) was heated under reflux for 3 h. The mixture was allowed to cool and then was poured into ice-cold water (100 g). The precipitate was collected by filtration and recrystallized from hexane to give derivatives 8a–c [20,26,27].
62% at 120℃; for 1 h; General procedure: A mixture of aryl amines (6 mmol) and EMME (6 mmol)was heated at 120 °C for 1–2 h. The mixture was thenevaporated to dryness to give a residue that was trituratedwith cyclohexane to give a solid that was filtered and driedto afford compound 2e–k. Diethyl 2-((phenylamino)methylene)malonate (2e) Starting from aniline (3 ml); Yield (white powder): 5 g(62 percent); m.p. 44–45 °C; IR (KBr) νmax 1400–1600(aromatic), 1660, 1690 (carbonyl) cm−1; LC-MS (ESI) m/z286.1 (M+Na+).
25 g at 20 - 55℃; for 3 h; In a clean round bottom flask charge aniline (10 gm), and di-ethyl (ethoxymethylene) malonate (2.40 gm). The reaction mass was heated to 50 55 C for 3.0 hr and cooled to 25-30 C. To this 80.0 ml of water was added. Again cool to 15-20 C and stir for 2.0 hr . Filter the product and wash with water to 25.0 gm title compound.Purity by HPLC - 98.78 percent.

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[13] ACS Medicinal Chemistry Letters, 2018,
[14] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5405 - 5418
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[20] Gazzetta Chimica Italiana, 1974, vol. 104, p. 715 - 729
[21] Justus Liebigs Annalen der Chemie, 1897, vol. 297, p. 77
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[29] Patent: US2008/306048, 2008, A1, . Location in patent: Page/Page column 17
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[51] Patent: WO2018/64632, 2018, A1, . Location in patent: Paragraph 00211; 00212
[52] Patent: US2017/96397, 2017, A1, . Location in patent: Paragraph 0091
[53] Patent: WO2018/107100, 2018, A1, . Location in patent: Paragraph 00230; 00231
[54] Patent: US2018/280349, 2018, A1, . Location in patent: Paragraph 0094-0095
  • 8
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  • 9
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[2] Patent: US2011/98311, 2011, A1,
  • 10
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  • 11
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  • 12
  • [ 4504-12-5 ]
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  • 13
  • [ 27971-92-2 ]
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  • 14
  • [ 122-51-0 ]
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  • 17
  • [ 1117-96-0 ]
  • [ 54535-12-5 ]
  • [ 54535-22-7 ]
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  • 18
  • [ 49597-05-9 ]
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[2] Chemische Berichte, 1894, vol. 27, p. 2744
  • 19
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  • [ 105-53-3 ]
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