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Chemical Structure| 10241-97-1 Chemical Structure| 10241-97-1

Structure of 10241-97-1

Chemical Structure| 10241-97-1

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Product Details of [ 10241-97-1 ]

CAS No. :10241-97-1
Formula : C10H9NO2
M.W : 175.18
SMILES Code : O=C(C(N1)=CC2=C1C=CC(C)=C2)O
MDL No. :MFCD00047166
InChI Key :DAITVOCMWPNFTL-UHFFFAOYSA-N
Pubchem ID :259188

Safety of [ 10241-97-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 10241-97-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 9
Fraction Csp3 0.1
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 50.22
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

53.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.39
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.67
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.17
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.38
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.99

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.05
Solubility 0.155 mg/ml ; 0.000882 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.44
Solubility 0.0641 mg/ml ; 0.000366 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.04
Solubility 0.159 mg/ml ; 0.00091 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.47 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.39

Application In Synthesis of [ 10241-97-1 ]

* 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.

  • Downstream synthetic route of [ 10241-97-1 ]

[ 10241-97-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 91462-34-9 ]
  • [ 10241-97-1 ]
  • 3
  • [ 10241-97-1 ]
  • [ 78-95-5 ]
  • 5-Methyl-1H-indole-2-carboxylic acid 2-oxo-propyl ester [ No CAS ]
  • 4
  • [ 10241-97-1 ]
  • [ 147539-21-7 ]
  • 1-[5-Methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 89 1-[5-Methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine (III) Following the general procedure of EXAMPLE 16 and making non-critical variations but starting with <strong>[10241-97-1]5-methylindole-2-carboxylic acid</strong> (0.23 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.29 g) and 1,1'-carbonyldiimidazole (0.21 g) the title compound is obtained, mp 199°-201°.
  • 5
  • [ 10241-97-1 ]
  • [ 614-96-0 ]
  • 7
  • [ 10241-97-1 ]
  • [ 39979-08-3 ]
  • 7-[(5-methyl-1<i>H</i>-indole-2-carbonyl)-amino]-heptanoic acid methyl ester [ No CAS ]
  • 8
  • [ 10241-97-1 ]
  • 7-amino-heptanoic acid benzyloxy-amide [ No CAS ]
  • 5-methyl-1<i>H</i>-indole-2-carboxylic acid (6-benzyloxycarbamoyl-hexyl)-amide [ No CAS ]
  • 9
  • [ 109-01-3 ]
  • [ 10241-97-1 ]
  • (5-methyl-1H-indol-2-yl)-(4-methylpiperazin-1-yl)methanone [ No CAS ]
  • 10
  • [ 10241-97-1 ]
  • [ 403860-64-0 ]
  • 5-methyl-1<i>H</i>-indole-2-carboxylic acid (1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-amide [ No CAS ]
  • 11
  • [ 29289-13-2 ]
  • [ 127-17-3 ]
  • [ 10241-97-1 ]
  • 12
  • [ 10241-97-1 ]
  • [ 123665-42-9 ]
  • [ 186430-35-3 ]
YieldReaction ConditionsOperation in experiment
Example 73 5-Methyl-1H-indole-2-carboxylic acid ((1S)-dimethylcarbamoyl-2-phenyl-ethyl)-amide (S)-2-Amino-N,N-dimethyl-3-phenyl-propionamide hydrochloride (1.0 mmol) and <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (1.0 mmol) were coupled according to Procedure A (0 - 25 °C reaction temperature). The crude product was triturated with 1:1 ether-hexanes and dried. Yield 302 mg, 87 percent; HPLC (60/40) 5.46 minutes (99 percent); mp 198.5 - 200 °C; PBMS 350 (MH+, 100 percent); Anal. Calcd for C21H23N3O2: C, 72.18; H, 6.63; N, 12.04. Found: C, 72,14; H, 6.90; N, 12.11.
  • 13
  • [ 10241-97-1 ]
  • 5-hydroxy-(1S)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole hydrochloride [ No CAS ]
  • [ 647021-90-7 ]
  • 15
  • [ 10241-97-1 ]
  • 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-methyl-1<i>H</i>-indole-2-carboxylic acid methyl ester [ No CAS ]
  • 16
  • [ 10241-97-1 ]
  • 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-methyl-1<i>H</i>-indole-2-carboxylic acid [ No CAS ]
  • 17
  • [ 10241-97-1 ]
  • 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-methyl-1H-indole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide [ No CAS ]
  • 18
  • [ 10241-97-1 ]
  • 7-[(5-methyl-1<i>H</i>-indole-2-carbonyl)-amino]-heptanoyl chloride [ No CAS ]
  • 19
  • [ 10241-97-1 ]
  • 7-[(5-methyl-1<i>H</i>-indole-2-carbonyl)-amino]-heptanoic acid [ No CAS ]
  • 20
  • [ 10241-97-1 ]
  • 5-methyl-1<i>H</i>-indole-2-carboxylic acid (6-hydroxycarbamoyl-hexyl)-amide [ No CAS ]
  • 21
  • [ 10241-97-1 ]
  • 4,6-Dimethyl-9H-pyrano[3,4-b]indol-1-one [ No CAS ]
  • 23
  • [ 10241-97-1 ]
  • [ 102870-03-1 ]
YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; sulfuric acid; In methanol; Preparation of Methyl 5-methylindole-2-carboxylate <strong>[10241-97-1]5-Methylindole-2-carboxylic acid</strong> (0.9 g, 5.13 mmol) was dissolved in methanol (25 ml) and treated with sulphuric acid (0.5 ml). The mixture was refluxed for 4 h. The volume of solvent was reduced and the residue treated with sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic fractions were dried and concentrated to give the desired ester.
  • 24
  • (+/-)-cis-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride [ No CAS ]
  • [ 10241-97-1 ]
  • (+/-)-cis-N1-[(5-Methylindol-2-yl)carbonyl]-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
[Example 114] (+-)-cis-N1-[(5-Methylindol-2-yl)carbonyl]-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride: The title compound was obtained from (+-)-cis-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride and <strong>[10241-97-1]5-methylindole-2-carboxylic acid</strong> in a similar manner to Example 6. 1H-NMR (DMSO-d6) delta: 1.35-1.50(2H,m), 1.50-1.80(4H,m), 1.85-2.07(2H,m), 2.36(3H,s),2.88(3H,s), 3.12(2H,br.s), 3.53(2H,br.s), 4.15-4.30(2H,m), 4.30-4.80(2H,br), 7.00(1H,dd,J=8.4,1.5Hz), 7.05(1H,d,J=1.5Hz)1 7.30(1H,d,J=8.4Hz), 7.38(1H,s), 8.00(1H,d,J=7.3Hz), 8.43(1H,br.s), 11.45(1H,br.s), 11.49(1H,br.s). MS (FAB) m/z: 452(M+H)+.
YieldReaction ConditionsOperation in experiment
(3) 5-Methyl-2-indolecarboxylic acid: 1H NMR (DMSO-d6) delta: 2.36 (3H, s), 6.98 (1H, dd, J=1.0, 2.0 Hz), 7.04-7.08 (1H, m), 7.30-7.33 (1H, m), 7.40 (1H, s), 11.6 (1H, br-s), 12.9 (1H, br-s).
  • 26
  • [ 10241-97-1 ]
  • [ 43115-40-8 ]
  • [ 783370-02-5 ]
YieldReaction ConditionsOperation in experiment
15% With triethanolamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; EXAMPLE 48 5-Methyl-1H-indole-2-carboxylic acid-(5-ethanesulfonyl-2-hydroxy-phenyl)-amide TEA (0.28 mL, 2.0 mmole) was added to a solution of <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (175 mg, 1.0 mmole), 2-amino-4-ethanesulfonyl-phenol (201 mg, 1.0 mmole), and BOP (442 mg, 1.0 mmole) in DMF (2.0 mL). The reaction mixture was shaken at room temperature overnight and then diluted with 1N hydrochloric acid (20 mL). The resulting precipitate was filtered off and washed with water. The residue was triturated with EtOAc (40 mL), the solvent was dried over magnesium sulfate, filtered, and reduced in volume while slowly adding hexanes until crystallization began. The crystalline product was filtered off and air-dried to afford the title compound as a brown powder (55 mg, 15percent yield). AP-/MS=359; AP-/MS=357.
  • 27
  • 2-methyl-1-(piperidin-4-yl)-2-propanol [ No CAS ]
  • [ 10241-97-1 ]
  • [ 1126084-35-2 ]
YieldReaction ConditionsOperation in experiment
71% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; General procedure: To a solution of <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (20) (263mg, 1.50mmol) in THF (7mL) were added 2-(piperidin-4-yl)ethanol (213mg, 1.65mmol), 1-hydroxybenzotriazole (HOBt, 101mg, 0.750mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC) hydrochloride (316mg, 1.65mmol), followed by stirring at room temperature for 14h. The reaction mixture was partitioned between ethyl acetate and 0.5M aqueous hydrochloric acid. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The residue was recrystallized from ethyl acetate/acetonitrile (5mL/2mL) to give 3 (365mg, 85.0percent) as a beige powder.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; Example 24 To a solution of 1800 mg of <strong>[10241-97-1]5-methylindole-2-carboxylic acid</strong> and 1500 mg of 2-methyl-1-(piperidin-4-yl)-2-propanol in 25 mL of DMF were added 2100 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride and 1500 mg of 1-hydroxybenzotriazole, followed by stirring at room temperature for 1 day. 0.5M aqueous hydrochloric acid was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with 0.5M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol = 1:0-10:1], and then crystallized from a mixture of ethyl acetate/diisopropyl ether to obtain 2140 mg of 2-methyl-1-{1-[(5-methyl-1H-indol-2-yl)carbonyl]piperidin-4-yl}propan-2-ol as a white crystal.
  • 28
  • [ 10241-97-1 ]
  • (S)-8-Chloromethyl-4-hydroxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester; hydrochloride [ No CAS ]
  • [ 1228694-06-1 ]
  • 29
  • [ 35161-71-8 ]
  • [ 10241-97-1 ]
  • [ 1250829-38-9 ]
  • 30
  • [ 10241-97-1 ]
  • [ 698-19-1 ]
  • [ 1263788-01-7 ]
  • 31
  • [ 10241-97-1 ]
  • [ 698-19-1 ]
  • [ 1263788-26-6 ]
  • 32
  • [ 10241-97-1 ]
  • [ 113258-86-9 ]
  • [ 1263787-87-6 ]
  • 33
  • [ 10241-97-1 ]
  • [ 113258-86-9 ]
  • [ 1263788-01-7 ]
  • 34
  • [ 10241-97-1 ]
  • [ 1278517-82-0 ]
  • 35
  • [ 10241-97-1 ]
  • [ 95538-31-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 0.25h;Reflux; Inert atmosphere; General procedure: Commercial indole-2-carboxylic acid was dissolved in thionyl chloride (1.5 mL/mmol) and the suspension was boiled for 15 min, during which time typically a dark green solution was formed. Excess thionyl chloride was removed under reduced pressure and the solid residue was suspended in toluene and the suspension was evaporated to dryness (toluene treatment was repeated three times). The green-grayish solid residues were used without further purification.
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; A vial was charged with 5-methyl-lH-indole-2-carboxylic acid (175 mg, 1.00 mmol, 1.00 equiv), DCM (10 mL) and oxalyl chloride (381 mg, 3.00 mmol, 3.00 equiv). N,N- Dimethylformamide (0.05 mL) was added at 0 °C. The resulting solution was stirred for 4 h at room temperature and concentrated under reduced pressure to provide 194 mg (crude) of 5- methyl-lH-indole-2-carbonyl chloride
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 10241-97-1 ]

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[ 10241-97-1 ]

Indoles

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