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[ CAS No. 289483-87-0 ] {[proInfo.proName]}

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Chemical Structure| 289483-87-0
Chemical Structure| 289483-87-0
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Product Details of [ 289483-87-0 ]

CAS No. :289483-87-0 MDL No. :MFCD09955317
Formula : C10H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :SHVBJIBHAKCNMY-UHFFFAOYSA-N
M.W : 171.20 Pubchem ID :11715247
Synonyms :

Calculated chemistry of [ 289483-87-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.38
TPSA : 65.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 1.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.33
Solubility : 0.806 mg/ml ; 0.00471 mol/l
Class : Soluble
Log S (Ali) : -2.43
Solubility : 0.631 mg/ml ; 0.00369 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0694 mg/ml ; 0.000406 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 289483-87-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 289483-87-0 ]

* 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 [ 289483-87-0 ]
  • Downstream synthetic route of [ 289483-87-0 ]

[ 289483-87-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 289483-82-5 ]
  • [ 289483-87-0 ]
YieldReaction ConditionsOperation in experiment
99.8% With hydrogen In tetrahydrofuran; methanol at 20℃; Reference Example 3A; Synthesis of 7-amino-3-cyano-4-methyl-1H-indole; After suspending 12.6 g (62.6 mmol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Reference Example 2A in a mixture of 100 mL of tetrahydrofuran and 100 mL of methanol, the suspension was subjected to hydrogenation in the presence of 430 mg (1.87 mmol) of platinum oxide at ordinary temperature, 3 atmospheres. The catalyst was removed by filtration, the filtrate was concentrated to dryness, and then a mixture of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration to give 10.7 g of the title compound (yield: 99.8percent). 1H-NMR (DMSO-d6) δ (ppm): 2.47 (3H, s), 5.07 (2H, s), 6.34 (1H, d, J=7.6Hz), 6.64 (1H, d, J=7.6Hz), 8.10 (1H, s), 11.70 (1H, br s).
84.8% With hydrogen In methanol; ethyl acetate at 20℃; After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10percent palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60°C, and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50°C for 16 hours to give 289 g of the title compound (yield: 84.8percent). HPLC analysis confirmed that the obtained compound was identical to the 7-amino-3-cyano-4-methyl-1H-indole described in WO00/50395.(HPLC conditions) Mobile phase: CH3CN/H2O/70percent HClO4 = 400/600/1 (v/v/v)Flow rate: 1.0 mL/minDetection: UV (282 nm)Column: YMC-Pack Pro C18 250 x 4.6 mm
84.8% With hydrogen In methanol; ethyl acetate at 20℃; Example 2A; Synthesis of 7-amino-3-cyano-4-methyl-1H-indole; After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10percent palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60° C., and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50° C. for 16 hours to give 289 g of the title compound (yield: 84.8percent). HPLC analysis confirmed that the obtained compound was identical to the 7-amino-3-cyano-4-methyl-1H-indole described in WO00/50395. (HPLC conditions) Mobile phase: CH3CN/H2O/70percent HClO4=400/600/1 (v/v/v) Flow rate: 1.0 mL/min Detection: UV (282 nm) Column: YMC-Pack Pro C18 250.x.4.6 mm
Reference: [1] Patent: US2007/37854, 2007, A1, . Location in patent: Page/Page column 6
[2] Patent: EP1666463, 2006, A1, . Location in patent: Page/Page column 10
[3] Patent: US2007/37854, 2007, A1, . Location in patent: Page/Page column 4
  • 2
  • [ 289483-82-5 ]
  • [ 289483-86-9 ]
  • [ 289483-87-0 ]
Reference: [1] Patent: EP1258252, 2002, A1,
[2] Patent: US2004/18192, 2004, A1,
  • 3
  • [ 289483-86-9 ]
  • [ 289483-87-0 ]
Reference: [1] Patent: US2002/128480, 2002, A1,
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