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[ CAS No. 494799-17-6 ] {[proInfo.proName]}

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Chemical Structure| 494799-17-6
Chemical Structure| 494799-17-6
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Product Details of [ 494799-17-6 ]

CAS No. :494799-17-6 MDL No. :MFCD09833286
Formula : C15H17NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OZJSQVKDKOOQIT-UHFFFAOYSA-N
M.W : 243.30 Pubchem ID :11241989
Synonyms :

Calculated chemistry of [ 494799-17-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 72.14
TPSA : 53.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 4.11
Log Po/w (WLOGP) : 3.91
Log Po/w (MLOGP) : 2.74
Log Po/w (SILICOS-IT) : 3.58
Consensus Log Po/w : 3.3

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.18
Solubility : 0.0162 mg/ml ; 0.0000667 mol/l
Class : Moderately soluble
Log S (Ali) : -4.93
Solubility : 0.00285 mg/ml ; 0.0000117 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.1
Solubility : 0.0193 mg/ml ; 0.0000794 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 494799-17-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 494799-17-6 ]

* 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 [ 494799-17-6 ]
  • Downstream synthetic route of [ 494799-17-6 ]

[ 494799-17-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 494799-16-5 ]
  • [ 494799-17-6 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogen In tetrahydrofuran; methanol for 14 h; Step 2; methy\\ 3-cvclohexyl-1H-indole-6-carboxylate; A solution (0.5 M) of 3-cyclohexenyl-1H-indole-6-carboxylic acid (from Step 1) in THF/M eOH (0.5 M, 1:1, v/v) was hydrogenated for 14 h over Pd(OH)2/C (0.1 eq., 20percent) at 60 psi. The catalyst was removed by filtration on a pad of celite.(TM). and the filtrate evaporated to dryness to afford 3-cyclohexyl-1 H-indoIe-6-carboxylic acid (90percent) as a white solid 1H NMR (300 MHz, DMSO-d6, 300 K) 6 1.20 -1.53 (m, SH), L70-L87 (m, 3H), 1.90-2.02 (m, 2H), 2.69-2.86 (m, 1H), 7.40 (s, 1H), 7.55-7.65 (rn, 2H), 8.0 (s, 1H), 11.40 (s, 1H); MS (ES+ m/z 244 (M+H)+. A solution of the foregoing compound in MeOH {0.4 M) was treated at 0 °C with thionylchloride (0.5 eq.) and refluxed for 24 h. Volatiles were removed under vacuum to afford the title compound (100percent) as a solid.
90% With ammonium formate In ethanol at 50℃; for 4 h; To a solution of 3-(1-cyclohexen-1-yl)-1 H-indole-6-carboxylic acid (Intermediate 60) (1 g, 4.1 mmol) in ethanol was added Pd/C 10percent (catalytic quantity) and ammonium formiate (2.6 g, 41 mmol). The mixture was stirred at 500C for 4 hours. A precipitate was formed, HCI 1 N was added until the precipitate was dissolved. The mixture was filtered on celite, the filtrate was evaporated. The residue was diluted with diethyl ether, washed with water. The organic phase was dried over Na2SO4, filtered and evaporated to give the title compound as beige solid (900 mg, 90percent). NMR1H NMR (300 MHz), , δ : 7.96 (s, 1 H), 7.57 (q, 2H), 7.28 (s, 1 H), 2.77 (m, 1 H), 1.96 (m, 1 H), 1.77 (m, 3H), 1.43 (m, 4H), 1.26 (m, 1 H).
87% With hydrogen In tetrahydrofuran; methanol at 20℃; for 3 h; Step B.A mixture of 1-2 (14.0 g, 58 mmol) and 20percent Pd(OH)2/C (600 mg) in methanol (50 mL) and THF (50 mL) was shaken in a hydrogenation apparatus under 55 psi pressure at room temperature for 3 h. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated to dryness. The residue was triturated in hexane, then the beige solid was collected by filtration, washed with hexane and dried under vacuum to give 12.3 g (87percent) of the target product 1-3: m/z : 244 (M+H)+.
83% With hydrogen In tetrahydrofuran; methanol; dichloromethane for 15 h; Step 4. 3-Cyclohexyl-1H-indole-6-carboxylic acid (164)[0310] Compound 163 from Step 3 (75.5g) was split into two batches. Each batches were suspended in 600 mL solvent (1:1 MeOH:THF). Pd catalyst (10percent on carbon, Ig / batch) was added as a slurry in CH2Cl2 (5 mL) and the mixture was hydrogenated for 15hr at 50-60 psi. The catalyst was filtered off by means of Celite and the solvents were removed via vacuum distillation to a give compound 164 as a yellow solid. Yield 63g (83percent).
79% With hydrogen In tetrahydrofuran; methanol at 20℃; for 18 h; 3-Cyclohexyl-1H-indole-6-carboxylic acid; 3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
79% With hydrogen In tetrahydrofuran; methanol at 20℃; for 18 h; 3-Cyclohexyl-1H-indole-6-carboxylic acid.; 3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
79% With hydrogen In tetrahydrofuran; methanol at 20℃; for 18 h; 3-Cyclohexyl-1H-indole-6-carboxylic acid. 3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
79% With hydrogen In tetrahydrofuran; methanol for 18 h; Parr bottle 3-cyclohexyl-1H-indole-6-carboxylic acid. Intermediate 3A (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The mixture was shaken under 55 psi of H2 for 18 hours. The catalyst was removed by filtration. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
79% With hydrogen In tetrahydrofuran; methanol at 20℃; for 18 h; 3-Cyclohexyl-1H-indole-6-carboxylic acid.; 3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
79% With hydrogen In tetrahydrofuran; methanol at 20℃; for 18 h; Intermediate 17 3-Cyclohexyl-1H-indole-6-carboxylic acid. 3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
79% With hydrogen In tetrahydrofuran; methanol at 20℃; for 18 h; 3-Cyclohexenyl-1H-indole-6-carboxylic acid (38 g) was added to a Parr bottle, followed by methanol (100 mL) and THF (100 mL). The bottle was flushed with argon and 10percent palladium on carbon (1.2 g) was added. The flask was then evacuated and subsequently refilled with H2 to a pressure of 55 psi, and the resultant mixture was shaken for 18 hours at RT. The catalyst was then removed by filtration through celite. Concentration of the filtrate provided the desired product as a pale purple solid (30.6 g, 79percent). ESI-MS m/z 244 (MH+).
78% With hydrogen In tetrahydrofuran; methanol for 20 h; The unsaturated derivative from above was hydrogenated for 20 h under 55 psi hydrogen gas pressure over 20percent Pd (OH) 2/C (10.25 g) using 1: 1 THF-MEOH (2.5 L) as solvent. After filtration of the catalyst, volatiles were removed under reduced pressure and the residue was triturated with hexane. The beige solid was collected by filtration, washed with hexane and dried under vacuum (356.4 g, 78percent yield).
50% With palladium 10% on activated carbon; ammonium formate In ethanol at 50℃; for 4 h; To a stirred solution of compound 34 (2 g, 8.29 mmol) in EtOH (20 mL) under argon atmosphere, 10percent Pd/C (200 mg) and ammonium formate (5.2 g, 82.9 mmol) was added. The reaction mass was stirred at 50 °C for 4 h. The progress of the reaction was monitored by TLC. After completion, the reaction mass cooled to RT, quenched with iN HC1 and ethyl acetate andfiltered through a pad of celite. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude. The crude compound was triturated with DCM to afford compound C19 (1 g, 50percent) as a light-brown solid. ‘H-NMR (400 MHz, DMSOd 6): ö 12.42 (s, 1H), 11.13 (s, 1H), 7.98 (s, 1H), 7.62—7.57 (m, 2H), 7.30 (s, 1H), 2.80—2.76 (m, 1H), 1.99 — 1.97 (m, 2H), 1.88 - 1.71 (m, 4H), 1.50 — 1.38 (m, 4H), LCMS Observed (m/z):244.05 (M+1).

Reference: [1] Patent: WO2006/29912, 2006, A1, . Location in patent: Page/Page column 21-22
[2] Patent: WO2009/147121, 2009, A1, . Location in patent: Page/Page column 65-66
[3] Patent: WO2009/80836, 2009, A2, . Location in patent: Page/Page column 56
[4] Patent: WO2006/76529, 2006, A1, . Location in patent: Page/Page column 135
[5] Patent: US2007/78122, 2007, A1, . Location in patent: Page/Page column 174
[6] Patent: US2007/60565, 2007, A1, . Location in patent: Page/Page column 70-71
[7] Patent: US2007/275947, 2007, A1, . Location in patent: Page/Page column 3; 32
[8] Patent: US2006/46983, 2006, A1, . Location in patent: Page/Page column 18; 38
[9] Patent: US2008/188458, 2008, A1, . Location in patent: Page/Page column 32-33
[10] Patent: US2008/171015, 2008, A1, . Location in patent: Page/Page column 23
[11] Patent: US2008/226592, 2008, A1, . Location in patent: Page/Page column 4; 36
[12] Patent: WO2004/65367, 2004, A1, . Location in patent: Page 110
[13] Patent: WO2018/53157, 2018, A1, . Location in patent: Page/Page column 162; 163
[14] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1314 - 1317
[15] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 4987 - 4993
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  • [ 50820-65-0 ]
  • [ 494799-17-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1314 - 1317
[2] Patent: WO2009/147121, 2009, A1,
[3] Organic Process Research and Development, 2018, vol. 22, # 10, p. 1393 - 1408
  • 3
  • [ 494799-18-7 ]
  • [ 494799-17-6 ]
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 10, p. 1393 - 1408
  • 4
  • [ 1670-82-2 ]
  • [ 494799-17-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 4987 - 4993
[2] Patent: US2008/188458, 2008, A1,
[3] Patent: US2008/171015, 2008, A1,
[4] Patent: US2008/226592, 2008, A1,
  • 5
  • [ 108-94-1 ]
  • [ 494799-17-6 ]
Reference: [1] Patent: WO2018/53157, 2018, A1,
[2] Patent: US2008/188458, 2008, A1,
[3] Patent: US2008/171015, 2008, A1,
[4] Patent: US2008/226592, 2008, A1,
[5] Organic Process Research and Development, 2018, vol. 22, # 10, p. 1393 - 1408
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