Home Cart 0 Sign in  
X

[ CAS No. 102308-97-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 102308-97-4
Chemical Structure| 102308-97-4
Chemical Structure| 102308-97-4
Structure of 102308-97-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 102308-97-4 ]

Related Doc. of [ 102308-97-4 ]

Alternatived Products of [ 102308-97-4 ]

Product Details of [ 102308-97-4 ]

CAS No. :102308-97-4 MDL No. :MFCD03839873
Formula : C9H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PGTSGPCXPIFQEL-UHFFFAOYSA-N
M.W : 146.19 Pubchem ID :2769564
Synonyms :

Calculated chemistry of [ 102308-97-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.6
TPSA : 30.95 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) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 1.77
Log Po/w (MLOGP) : 1.23
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 1.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.337 mg/ml ; 0.00231 mol/l
Class : Soluble
Log S (Ali) : -2.32
Solubility : 0.703 mg/ml ; 0.00481 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.46
Solubility : 0.502 mg/ml ; 0.00344 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 102308-97-4 ]

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

Application In Synthesis of [ 102308-97-4 ]

* 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 [ 102308-97-4 ]
  • Downstream synthetic route of [ 102308-97-4 ]

[ 102308-97-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 29906-67-0 ]
  • [ 102308-97-4 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; 10percent Pd/C (0.18 g/g of startingmaterial) was added to a solution of starting material dissolved inTHF (54 mL/g of starting material). Reaction flask was sealed andvacuum was used to remove air. A balloon filled with hydrogen gaswas then attached to the flask. The reaction was stirred at roomtemperature for 24e48 h or until disappearance of starting materialwas observed by TLC. The reaction was then filtered through celite.Filtrate was rotovapped to give a brown solid; 100percent; 1H NMR(DMSO): δ 7.15-7.05 (m, 2H), 6.71 (dd, J 3.0, 0.9 Hz, 1H), 6.57 (dd,J 8.5, 2.1 Hz, 1H), 6.12 (dd, J 3.0, 0.9 Hz, 1H), 3.67 (s, 3H); 13CNMR (DMSO): δ141.30, 131.12, 129.49, 129.44, 129.41, 112.31, 110.11,104.21, 99.13, 32.86.
95.8% With iron; acetic acid In ethanol at 78℃; for 1 h; 1-Methyl-5-nitro -1H- indole (270mg, 1mmol), Fe powder (1.12g, 20mmol, 10equiv) was added ethanol (15ml) and glacial acetic acid (2ml) in, 78 heated at reflux for 1h, TLC monitoring. After completion of the reaction, it was filtered through Celite, washed with ethanol to precipitate a colorless, ethanol rotary evaporation. The solid was dissolved in ethyl acetate followed by the addition, ultrasonic minutes, extracted with saturated NaHCO3 wash, water, NaCl wash, saturated MgSO4 dry. The organic layer by rotary evaporation, dried, the crude product was purified by column chromatography to give 230mg of yellow product, 1-methyl-5-amino-1H- indole, yield 95.8percent.
95.5% With palladium on activated charcoal; hydrogen In ethanol at 50℃; for 5 h; A2 (1.0 g, 5.7 mmol) was dissolved in ethanol and catalyzed with Pd/C and H2 for 5 hours at 50°C. The catalyst was filtered off and the solvent was removed to give 0.85 g of A3. The yield in this step was 95.5percent without further purification.
81% With hydrazine hydrate In ethanol at 80℃; for 1 h; Inert atmosphere General procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.
77% With hydrogen In tetrahydrofuran; ethanol for 4 h; Step G: Synthesis of 1 -methyl- lH-indol-5 -amine as an intermediate <n="38"/>; [0100] A mixture of l-methyl-5-nitro-lH-indole (2.00 g, 11.3 mmol) and platinum (IV) oxide (0.20 g, 10percent by weight) in a mixture of ethanol (20 mL) and tetrahydrofuran (20 mL) was shaken under an atmosphere of hydrogen at 40 psi for 4 h. After this time, the mixture was filtered through diatomaceous earth and concentrated under reduced pressure. Purification by flash chromatography (silica, 1 :3, ethyl acetate/hexanes) afforded 1-methyl- lH-indol-5-amine (1.28g, 77percent) as a red oil: 1H NMR (500 MHz, CDCl3) δ 7.12 (d, J= 8.5 Hz, IH), 6.95 (d, J= 3.0 Hz, IH), 6.92 (d, J= 2.0 Hz, IH), 6.69 (dd, J= 2.0, 8.5 Hz, IH), 6.28 (d, J= 3.0 Hz, IH), 3.72 (s, 3H), 3.47 (bs, 2H).
27% With tin(ll) chloride In ethyl acetate at 20℃; To l-methyl-5-nitro-lH-indole (0.5g, 2.84mmol) in ethyl acetate (10ml), tin (II) chloride hydrate (2.5g, 11.4mmol, 4eq) was added and the reaction mixture stirred overnight at room temperature. The reaction mixture was basified with aqueous sodium EPO <DP n="50"/>hydroxide solution (pH 8) and the compound extracted using ethyl acetate. The crude compound obtained was purified by column chromatography over silica gel using ethyl acetate/ hexane (1:1) as eluent to give 1 -methyl- lH-indol-5ylamine (120mg, 27percent).

Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1202 - 1213
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 10, p. 3531 - 3541
[3] New Journal of Chemistry, 2015, vol. 39, # 7, p. 5360 - 5365
[4] Patent: CN104163815, 2017, B, . Location in patent: Paragraph 0065; 0066; 0068
[5] Patent: CN107163029, 2017, A, . Location in patent: Paragraph 0049; 0053; 0054; 0055; 0056; 0057; 0058
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1461 - 1464
[7] Catalysis Communications, 2016, vol. 84, p. 25 - 29
[8] Patent: WO2009/42907, 2009, A1, . Location in patent: Page/Page column 36-37
[9] Synthetic Communications, 1998, vol. 28, # 1, p. 147 - 157
[10] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
[11] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 48-49
[12] Journal of Medicinal Chemistry, 1993, vol. 36, # 8, p. 1104 - 1107
[13] Organic Letters, 2004, vol. 6, # 17, p. 2897 - 2900
[14] Archiv der Pharmazie, 2005, vol. 338, # 2-3, p. 67 - 73
[15] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8050 - 8057
[16] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5509 - 5513
[17] Patent: WO2006/40520, 2006, A1, . Location in patent: Page/Page column 125-126
[18] Patent: US2011/190299, 2011, A1, . Location in patent: Page/Page column 22-23
[19] Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504
[20] Patent: CN106349241, 2017, A, . Location in patent: Paragraph 0571; 0572; 0573; 0574
  • 2
  • [ 6146-52-7 ]
  • [ 102308-97-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 10, p. 3531 - 3541
[2] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8050 - 8057
[3] Archiv der Pharmazie, 2005, vol. 338, # 2-3, p. 67 - 73
[4] Organic Letters, 2004, vol. 6, # 17, p. 2897 - 2900
[5] Synthetic Communications, 1998, vol. 28, # 1, p. 147 - 157
[6] Journal of Medicinal Chemistry, 1993, vol. 36, # 8, p. 1104 - 1107
[7] Patent: US2011/190299, 2011, A1,
[8] Patent: WO2006/123145, 2006, A1,
[9] Patent: CN107163029, 2017, A,
[10] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1202 - 1213
  • 3
  • [ 10075-52-2 ]
  • [ 102308-97-4 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 18, p. 4528 - 4533
  • 4
  • [ 6146-52-7 ]
  • [ 74-88-4 ]
  • [ 102308-97-4 ]
Reference: [1] Patent: US2003/195201, 2003, A1,
  • 5
  • [ 67-56-1 ]
  • [ 29906-67-0 ]
  • [ 102308-97-4 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
  • 6
  • [ 67-56-1 ]
  • [ 29906-67-0 ]
  • [ 102308-97-4 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
  • 7
  • [ 67-56-1 ]
  • [ 29906-67-0 ]
  • [ 108-98-5 ]
  • [ 102308-97-4 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
  • 8
  • [ 131013-67-7 ]
  • [ 102308-97-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 317,322; engl. Ausg. S. 322, 326
  • 9
  • [ 824-21-5 ]
  • [ 102308-97-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 317,322; engl. Ausg. S. 322, 326
  • 10
  • [ 64180-07-0 ]
  • [ 102308-97-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 317,322; engl. Ausg. S. 322, 326
  • 11
  • [ 108981-60-8 ]
  • [ 102308-97-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 317,322; engl. Ausg. S. 322, 326
  • 12
  • [ 106883-07-2 ]
  • [ 102308-97-4 ]
Reference: [1] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 317,322; engl. Ausg. S. 322, 326
Recommend Products
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 102308-97-4 ]

Zafirlukast Related Intermediates

Chemical Structure| 29906-67-0

[ 29906-67-0 ]

1-Methyl-5-nitro-1H-indole

Related Functional Groups of
[ 102308-97-4 ]

Amines

Chemical Structure| 132-32-1

[ 132-32-1 ]

9-Ethyl-9H-carbazol-3-amine

Similarity: 0.92

Chemical Structure| 884507-17-9

[ 884507-17-9 ]

(1-Methyl-1H-indol-5-yl)methanamine

Similarity: 0.92

Chemical Structure| 5192-03-0

[ 5192-03-0 ]

1H-Indol-5-amine

Similarity: 0.92

Chemical Structure| 5318-27-4

[ 5318-27-4 ]

6-Aminoindole

Similarity: 0.89

Chemical Structure| 26807-73-8

[ 26807-73-8 ]

1-Benzyl-1H-indol-5-amine

Similarity: 0.88

Related Parent Nucleus of
[ 102308-97-4 ]

Indoles

Chemical Structure| 16096-33-6

[ 16096-33-6 ]

1-Phenyl-1H-indole

Similarity: 0.97

Chemical Structure| 40876-94-6

[ 40876-94-6 ]

1-Ethyl-2-methyl-1H-indole

Similarity: 0.97

Chemical Structure| 884507-17-9

[ 884507-17-9 ]

(1-Methyl-1H-indol-5-yl)methanamine

Similarity: 0.92

Chemical Structure| 5192-03-0

[ 5192-03-0 ]

1H-Indol-5-amine

Similarity: 0.92

Chemical Structure| 120-72-9

[ 120-72-9 ]

1H-Indole

Similarity: 0.92