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[ CAS No. 128717-77-1 ] {[proInfo.proName]}

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Chemical Structure| 128717-77-1
Chemical Structure| 128717-77-1
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Product Details of [ 128717-77-1 ]

CAS No. :128717-77-1 MDL No. :MFCD05664009
Formula : C10H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MSALXMDIYCKASR-UHFFFAOYSA-N
M.W : 191.18 Pubchem ID :15067967
Synonyms :

Calculated chemistry of [ 128717-77-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.75
TPSA : 62.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.8
Log Po/w (SILICOS-IT) : 1.87
Consensus Log Po/w : 1.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.863 mg/ml ; 0.00451 mol/l
Class : Soluble
Log S (Ali) : -2.47
Solubility : 0.65 mg/ml ; 0.0034 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.312 mg/ml ; 0.00163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 128717-77-1 ]

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 [ 128717-77-1 ]

* 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 [ 128717-77-1 ]

[ 128717-77-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 128717-76-0 ]
  • [ 128717-77-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-methoxy-3-[(trifluoromethyl)carbonyl]-1H-indole With sodium hydroxide In water for 1h; Heating / reflux; Alkaline conditions; Stage #2: With hydrogenchloride In water Acidic aqueous solution; Example 1 Example 1. 1-[1-(Cyclohexylmethyl)-7-methoxy-1H-indol-3-yl]carbonyl}-4-ethylpiperazine, maleic acid salt Example 1 1-[1-(Cyclohexylmethyl)-7-methoxy-1H-indol-3-yl]carbonyl}-4-ethylpiperazine, maleic acid salt To a solution of 7-methoxyindole (3.5 g, 23.8 [MMOL)] in dimethylformamide (35 ml) at [0°C] was added trifluoroacetic anhydride (4.4 [ML,] 31.5 [MMOL)] over 5 minutes. The mixture was stirred at room temperature for 1 h, then poured into water [(200] [ML).] The resulting [7-METHOXY-3-[(TRIFLUOROMETHYL) CARBONYL] INDOLE] precipitate was filtered off, washing with water and used directly in the next step. The damp solid was suspended in 4 M sodium hydroxide solution (140 [ML)] and heated to reflux with stirring for 1 h. The mixture was cooled and washed twice with diethyl ether. The aqueous phase was then acidified to pH 1 using 5 M hydrochloric acid and the resulting fine precipitate filtered off, washed with water and dried to afford 7-methoxyindole-3-carboxylic acid (3.6 g). 7-Methoxyindole-3-carboxylic acid (3.0 g, 16.6 [MMOL)] was added portionwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 1.56 g, [39MMOL)] in dimethylformamide (75 [ML).] After 1 h, [BROMOMETHYLCYCLOHEXANE] (5.7 g, 32.3 [MMOL)] was added. The mixture was heated to [60°C] with stirring for 1 h. The mixture was diluted with water (250 ml) and washed with ethyl acetate and then diethyl ether. The aqueous phase was acidified to pH 1 using 5 [M] hydrochloric acid and the precipitate filtered off. The crude product was recrystallised from ethyl acetate to afford [1-] (cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (3.75 g) as a crystalline solid. To a solution of 1- (cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (2.5 g, 8.8 [MMOL)] in THF (30 [ML)] was added [OXALYL] chloride (4.5 g, 35.3 [MMOL),] dropwise with stirring. The mixture was stirred at room temperature for 18 h. The volatile components were evaporated under reduced pressure to afford 1- (cyclohexylmethyl)- 7-methoxyindole-3-carbonyl chloride (2.7 g) as a crystalline solid. To [1- (CYCLOHEXYIMETHYL)-7-METHOXYINDOLE-3-CARBONYL CHLORIDE] (1.9 g, 6.2 [MMOL)] was added a solution of N-ethylpiperazine (1.35 g, 11.8 [MMOL)] in [DICHLOROMETHANE] (60 [ML).] The mixture was stirred until the acid chloride dissolved. Triethylamine (3 [ML,] 21.5 mmol was added and the solution stirred at room temperature for 18 h. The reaction mixture was washed with water (2 x 50 [ML),] dried with sodium sulfate and evaporated to afford an oil. This was purified by flash chromatography eluting with 0- 10% (v/v) methanol in dichloromethane to afford the title compound (free base) as a [GUM.] The free base was dissolved in diethyl ether (50 [ML)] and filtered into a stirred solution of maleic acid (0.83 g, 7.15 [MMOL)] in ether (24 [ML)] and methanol (4 [ML).] The resulting mixture was stirred for 30 minutes and the solid filtered off. The solid was re- crystallised from methanol/diethyl ether to afford title compound (1: 1 maleic acid salt) as a crystalline solid (2.7 g, 5.4 [MMOL). 1H] NMR [(400MHZ,] CD30D) aH 0.99-1. 08 (2H, m), 1.12-1. 25 (3H, m), 1.36 (3H, t, J 7.5), 1.56 (2H, d, J 12.5), 1.63-1. 74 (3H, m), 1.77-1. 89 (1 H, m), 3.22 (2H, q, [J 7.] 5), 3.30-3. 35 (4H, m), 3.95 (3H, s), 3. 90-4. 05 (4H, m), 4.25 (2H, d, [J 7.] 0), 6.25 (2H, s, maleat) 6.76 (1H, d, [J 7.] 5), 7.10 (1H, t, [J 7.] 5), 7.26 (1 H, d, [J 7.] 5), 7.53 (1H, s); EIMS : m/z = 384.4 [[M+H] +.]
Stage #1: 7-methoxy-3-[(trifluoromethyl)carbonyl]-1H-indole With lithium hydroxide In water for 2h; Heating / reflux; Stage #2: With hydrogenchloride In water 1 The damp solid was suspended in 4 M aqueous sodium hydroxide (1700 mi) and heated to reflux with stirring for 2 h. The mixture was cooled and washed with diethyl ether (2 x 400 ml). The aqueous phase was then acidified to pH 1 using 5 M hydro- chloric acid and the resulting fine precipitate filtered off, washed with water to neutral- ity and dried to afford 7-methoxy-1 H-indole-3-carboxylic acid as a pink solid (42.7 g).
  • 2
  • [ 128717-77-1 ]
  • [ 944086-18-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-Methoxyindole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: With ammonia In water; N,N-dimethyl-formamide 7-methoxy-l//-indole-3-carbonitrile[0246] To a solution of 7-methoxy-l//-indole-3-carboxylic acid (363 mg, 1.90 mmol) in DMF (10 mL) was added carbonyl diimidazole (382 mg, 2.36 mmol) in one portion. After stirring at room temperature for Ih 30 min 28% aqueous NH3 (0.50 mL, approx. 7 mmol) was added, and the mixture was left stirring overnight. After evaporation to dryness the remanens was taken up in EtOAc (200 mL) and the organic layer was washed with H2O (2x 10 mL), saturated aqueous NaHCC>3 (10 mL), brine, dried over Na2SO4 and evaporated to dryness to give the intermediate amide (527 mg). This amide was dissolved in a mixture of CH3CN (15 mL) and H2O (15 mL). The mixture was heated to 50 0C and Pd(OAc)2 (408 mg, 1.81 mmol) was added in portions over 24 h. The black reaction mixture was quenched with saturated aqueous NaHCO3 (25 mL) and the CH3CN was removed by rotary evaporation. The remaining aqueous layer was extracted with EtOAc (3x 25 mL). The combined organic layers washed with brine, dried over Na2SO4 and evaporated to dryness to give the pure title compound (134 mg, 41% overall yield.).[0247] One peak GC-MS m/z (relative intensity) 172(100), 157(67), 129(60), 102(1 1).
  • 3
  • [ 128717-77-1 ]
  • [ 2550-36-9 ]
  • [ 639067-81-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-Methoxyindole-3-carboxylic acid With sodium hydride In DMF (N,N-dimethyl-formamide) for 1h; Stage #2: Cyclohexylmethyl bromide In DMF (N,N-dimethyl-formamide) at 60℃; for 1h; Stage #3: With hydrogenchloride In water Acidic aqueous solution; Example 1 Example 1. 1-[1-(Cyclohexylmethyl)-7-methoxy-1H-indol-3-yl]carbonyl}-4-ethylpiperazine, maleic acid salt Example 1 1-[1-(Cyclohexylmethyl)-7-methoxy-1H-indol-3-yl]carbonyl}-4-ethylpiperazine, maleic acid salt To a solution of 7-methoxyindole (3.5 g, 23.8 [MMOL)] in dimethylformamide (35 ml) at [0°C] was added trifluoroacetic anhydride (4.4 [ML,] 31.5 [MMOL)] over 5 minutes. The mixture was stirred at room temperature for 1 h, then poured into water [(200] [ML).] The resulting [7-METHOXY-3-[(TRIFLUOROMETHYL) CARBONYL] INDOLE] precipitate was filtered off, washing with water and used directly in the next step. The damp solid was suspended in 4 M sodium hydroxide solution (140 [ML)] and heated to reflux with stirring for 1 h. The mixture was cooled and washed twice with diethyl ether. The aqueous phase was then acidified to pH 1 using 5 M hydrochloric acid and the resulting fine precipitate filtered off, washed with water and dried to afford 7-methoxyindole-3-carboxylic acid (3.6 g). 7-Methoxyindole-3-carboxylic acid (3.0 g, 16.6 [MMOL)] was added portionwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 1.56 g, [39MMOL)] in dimethylformamide (75 [ML).] After 1 h, [BROMOMETHYLCYCLOHEXANE] (5.7 g, 32.3 [MMOL)] was added. The mixture was heated to [60°C] with stirring for 1 h. The mixture was diluted with water (250 ml) and washed with ethyl acetate and then diethyl ether. The aqueous phase was acidified to pH 1 using 5 [M] hydrochloric acid and the precipitate filtered off. The crude product was recrystallised from ethyl acetate to afford [1-] (cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (3.75 g) as a crystalline solid. To a solution of 1- (cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (2.5 g, 8.8 [MMOL)] in THF (30 [ML)] was added [OXALYL] chloride (4.5 g, 35.3 [MMOL),] dropwise with stirring. The mixture was stirred at room temperature for 18 h. The volatile components were evaporated under reduced pressure to afford 1- (cyclohexylmethyl)- 7-methoxyindole-3-carbonyl chloride (2.7 g) as a crystalline solid. To [1- (CYCLOHEXYIMETHYL)-7-METHOXYINDOLE-3-CARBONYL CHLORIDE] (1.9 g, 6.2 [MMOL)] was added a solution of N-ethylpiperazine (1.35 g, 11.8 [MMOL)] in [DICHLOROMETHANE] (60 [ML).] The mixture was stirred until the acid chloride dissolved. Triethylamine (3 [ML,] 21.5 mmol was added and the solution stirred at room temperature for 18 h. The reaction mixture was washed with water (2 x 50 [ML),] dried with sodium sulfate and evaporated to afford an oil. This was purified by flash chromatography eluting with 0- 10% (v/v) methanol in dichloromethane to afford the title compound (free base) as a [GUM.] The free base was dissolved in diethyl ether (50 [ML)] and filtered into a stirred solution of maleic acid (0.83 g, 7.15 [MMOL)] in ether (24 [ML)] and methanol (4 [ML).] The resulting mixture was stirred for 30 minutes and the solid filtered off. The solid was re- crystallised from methanol/diethyl ether to afford title compound (1: 1 maleic acid salt) as a crystalline solid (2.7 g, 5.4 [MMOL). 1H] NMR [(400MHZ,] CD30D) aH 0.99-1. 08 (2H, m), 1.12-1. 25 (3H, m), 1.36 (3H, t, J 7.5), 1.56 (2H, d, J 12.5), 1.63-1. 74 (3H, m), 1.77-1. 89 (1 H, m), 3.22 (2H, q, [J 7.] 5), 3.30-3. 35 (4H, m), 3.95 (3H, s), 3. 90-4. 05 (4H, m), 4.25 (2H, d, [J 7.] 0), 6.25 (2H, s, maleat) 6.76 (1H, d, [J 7.] 5), 7.10 (1H, t, [J 7.] 5), 7.26 (1 H, d, [J 7.] 5), 7.53 (1H, s); EIMS : m/z = 384.4 [[M+H] +.]
Stage #1: 7-Methoxyindole-3-carboxylic acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 15℃; for 1.83333h; Stage #2: Cyclohexylmethyl bromide In DMF (N,N-dimethyl-formamide) at 60℃; for 3h; Stage #3: With hydrogenchloride In water 1 To a solution of 7-methoxy-1H-indole-3-carboxylic acid (42.7 g, 224 mmol) in di- methylformamide (1250 mi) at 10°C under nitrogen was added sodium hydride (60% dispersion in mineral oil, 23.0 g, 575 mmol) portionwise over 20 minutes, maintaining the temperature below 15°C. The cooling bath was removed and the suspension stirred for 90 minutes. Cyclohexylmethyl bromide (64.7 mi, 464 mmol) was added. The mixture was heated at 60°C with stirring for 3 h. The mixture was cooled to 10°C and poured into water (3600 ml). The emulsion was washed with diethyl ether (3 x 500 ml). The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off, washed with water to neutrality and dried to afford 1-(cyclo- hexyl) methyl-7-methoxy-1H-indole-3-carboxpic acid (55 g) as a white solid.
  • 4
  • [ 128717-77-1 ]
  • [ 128717-78-2 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25℃; for 2h; Inert atmosphere; 65.1 Step 1: Indole acid was taken in a 10 mL round-bottom flask under nitrogen atmosphere. Dichloromethane (10 mL/mmol) was added to it. The reaction mixture was cooled. Oxalyl chloride (freshly distilled, 1.5 eq.) and 1 drop of DMF was added to it. Reaction mixture was stirred at 25° C. for 2 hr. Formation of acid chloride was monitored by quenching an aliquot with methanol and comparing the formation of the methyl ester with respect to the indole acid. The solvent was evaporated under reduced pressure and the residue was used directly for step 2.
  • 5
  • [ 128717-77-1 ]
  • [ 22746-09-4 ]
  • [ 2488932-81-4 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 7-Methoxyindole-3-carboxylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide In ethyl acetate at 23℃; for 1h; Inert atmosphere; Stage #2: 4,6-dimethyl-2-(piperazin-1-yl)pyrimidine In ethyl acetate at 50℃; for 3h; Inert atmosphere; General procedure for the coupling reactions to obtain compounds 5-8 and 13-25. General procedure: Toa suspension of indole acid and EDC.HCl were added EtOAc and two drops of DMF, and themixture was stirred for 1 h at 23°C followed by the addition of compound 4. The reaction washeated at 50°C for 3 h, and solvents were evaporated to dryness under high vacuum. Waterwas added, sonicated, and filtered. The filter cake was washed with hexane/EtOAc and furtherpurified by crystallization from MeOH/EtOH/Et2O/EtOAc.
  • 6
  • [ 128717-77-1 ]
  • [ 939-26-4 ]
  • [ 2171522-06-6 ]
YieldReaction ConditionsOperation in experiment
1.66 g With sodium hydride In N,N-dimethyl-formamide; mineral oil at 50 - 60℃; for 1h; 58 7-Methoxy-1-(2-naphthylmethyl)-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-3,6- bis(hydroxymethyl)tetrahydropyran-3-yl]indole-3-carboxamide To a solution of 7-methoxy-1H-indole-3-carboxylic acid (1.0 g, 5.23 mmol) in dry DMF (10 mL) was added slowly sodium hydride (60% dispersion in mineral oil, 628 mg, 15.69 mmol). To this mixture was added 2-(bromomethyl)naphthalene (1.27 g, 5.75 mmol), and the reaction mixture was heated to 50-60 ^C for 1 hr. The mixture was then cooled to rt and poured onto crushed ice and acidified with 2 N aqueous HCl to pH 6. The precipitate was collected, washed with water and dried to give 7-methoxy-1-(2-naphthylmethyl)indole-3- carboxylic acid (1.66 g).
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