[ CAS No. 5192-04-1 ]

Name: 5192-04-1|1H-Indol-7-amine|95%
Brand: Ambeed
SKU: A235435
Price: 8.0 USD
Availability: InStock
Rating: 94 (40 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 5192-04-1

Structure of 5192-04-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 5192-04-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5192-04-1 ]

SDS Specification

Alternatived Products of [ 5192-04-1 ]

Product Details of [ 5192-04-1 ]

CAS No. :	5192-04-1	MDL No. :	MFCD02093960
Formula :	C₈H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WTFWZOSMUGZKNZ-UHFFFAOYSA-N
M.W :	132.16	Pubchem ID :	111634
Synonyms :

Calculated chemistry of [ 5192-04-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.7
TPSA :	41.81 Å²

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) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.07
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	1.76
Log Po/w (MLOGP) :	0.91
Log Po/w (SILICOS-IT) :	1.86
Consensus Log Po/w :	1.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	0.856 mg/ml ; 0.00648 mol/l
Class :	Soluble
Log S (Ali) :	-1.85
Solubility :	1.86 mg/ml ; 0.0141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.89
Solubility :	0.171 mg/ml ; 0.00129 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.21

Safety of [ 5192-04-1 ]

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 [ 5192-04-1 ]

* 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.

Upstream synthesis route of [ 5192-04-1 ]
Downstream synthetic route of [ 5192-04-1 ]

[ 5192-04-1 ] Synthesis Path-Upstream 1~13

1
[ 6960-42-5 ]
[ 5192-04-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With ammonium formate In ethanol for 1 h; Heating / reflux	By following the procedures as described in Preparation 7 (Scheme VII, Step A) 7-nitro indole is dissolved in ethanol and. to this mixture added ammonium formate (lOeq) and a catalytic amount of 10percent palladium on carbon. This mixture is then heated to reflux for 1 hr before it is cooled, filtered through celite and evaporated to provide the product as a purple solid (99percent).
99%	With ammonium formate In ethanol for 1 h; Heating / reflux	lH-Indol-7-ylamine Dissolve 7-nitroindole in ethanol and add ammonium formate (10 equivalents) and a catalytic amount of 10percent palladium on carbon. Heat the mixture to reflux for 1 hr before cooling, filter through celite, and evaporate to provide the product as a purple solid (99percent).
99%	With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 20℃; for 12 h; Schlenk technique	General procedure: Procedure B: A mixture of nitro compounds 1 (0.50 mmol) and Pd/C (10 wtpercent palladium on activated carbon paste and 50 percent moisture, 5 wtpercent wet Pd/C based on starting material 1) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and stirred at room temperature. Followed by addition of H₂NNH₂·H₂O (50 mg, 1.0 mmol, 2.0 equiv) and the mixture was stirred at room temperature until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.

96.7%

With hydrogen In ethanol at 27℃;

1H-Indol-7-ylamine Charge a 3-gal autoclave with 7-nitroindole (250 g, 1.542 moles), 2B-3 ethyl alcohol (5.0 L), and 10 percent Pd/C (50.0 g). Stir at 50 psi H2 for 2 h at <27 °C. When the reaction is deemed complete, filter the reactor contents through Celite followed by concentration of the filtrate to dryness to yield 197.0 g (96.7 percent) of the title compound as purple solid. IH- NMR (CD30D, 300MHz) 8 7.16 (d, 1H), 7.00 (dd, 1H), 6.81 (t, 1H), 6.50 (dd, 1H), 6.37 (d, 1H).

Reference： [1] Patent: WO2004/67529, 2004, A1, . Location in patent: Page 75 - 76
[2] Patent: WO2005/92854, 2005, A1, . Location in patent: Page/Page column 53
[3] Green Chemistry, 2017, vol. 19, # 3, p. 809 - 815
[4] Synthetic Communications, 2018, vol. 48, # 19, p. 2475 - 2484
[5] Patent: WO2005/92854, 2005, A1, . Location in patent: Page/Page column 56-57
[6] Tetrahedron Letters, 1995, vol. 36, # 14, p. 2411 - 2414
[7] European Journal of Organic Chemistry, 2009, # 28, p. 4854 - 4866
[8] Tetrahedron, 2008, vol. 64, # 3, p. 568 - 574
[9] Organic and Biomolecular Chemistry, 2014, vol. 13, # 3, p. 925 - 937
[10] Journal of Medicinal Chemistry, 1995, vol. 38, # 11, p. 1942 - 1954
[11] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3789 - 3799
[12] Journal of Medicinal Chemistry, 2002, vol. 45, # 22, p. 4913 - 4922
[13] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6443 - 6445
[14] Patent: US2004/63733, 2004, A1,
[15] Chemical Communications, 2009, # 41, p. 6279 - 6281
[16] Patent: EP2366687, 2011, A2, . Location in patent: Page/Page column 24-25
[17] Organic and Biomolecular Chemistry, 2012, vol. 10, # 30, p. 5909 - 5915
[18] Patent: WO2012/115479, 2012, A2, . Location in patent: Page/Page column 19-20
[19] Organic Letters, 2013, vol. 15, # 18, p. 4730 - 4733
[20] Synthesis (Germany), 2015, vol. 47, # 6, p. 861 - 870
[21] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837
[22] European Journal of Organic Chemistry, 2018, vol. 2018, # 2, p. 209 - 214
[23] RSC Advances, 2018, vol. 8, # 16, p. 8898 - 8909
[24] Applied Catalysis A: General, 2018, vol. 559, p. 127 - 137

2
[ 51417-51-7 ]
[ 5192-04-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
[2] Patent: EP1813602, 2007, A1, . Location in patent: Page/Page column 6-7

3
[ 96831-52-6 ]
[ 5192-04-1 ]

Reference： [1] Patent: US4506078, 1985, A,

4
[ 4129-17-3 ]
[ 61149-50-6 ]
[ 5192-04-1 ]

Reference： [1] Patent: US2004/18192, 2004, A1,

5
[ 2942-37-2 ]
[ 5192-04-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 3, p. 726 - 738

6
[ 81524-76-7 ]
[ 5192-04-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226

7
[ 6960-46-9 ]
[ 5192-04-1 ]

Reference： [1] Patent: EP2366687, 2011, A2,
[2] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837

8
[ 6960-45-8 ]
[ 5192-04-1 ]

Reference： [1] Patent: EP2366687, 2011, A2,
[2] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837

9
[ 528-29-0 ]
[ 5192-04-1 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 18, p. 4730 - 4733

10
[ 292853-66-8 ]
[ 5192-04-1 ]

Reference： [1] Patent: EP2366687, 2011, A2,

11
[ 577-19-5 ]
[ 5192-04-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226

12
[ 253-66-7 ]
[ 5192-04-1 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 3, p. 726 - 738

13
[ 6293-87-4 ]
[ 5192-04-1 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 24, p. 4830 - 4837

[ 5192-04-1 ] Synthesis Path-Downstream 1~68

1
[ 2942-37-2 ]
[ 5192-04-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 726 - 738

2
[ 3987-53-9 ]
[ 5192-04-1 ]
4-Benzyl-1-(1H-indol-7-yl)-piperazine-2,6-dione [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1988,vol. 107,p. 303 - 310

3
[ 656227-56-4 ]
[ 5192-04-1 ]
5-{1-[(1H-indol-7-ylcarbamoyl)-methyl]-1H-pyrazol-3-yl}-thiophene-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 370 - 375

4
[ 5192-04-1 ]
1-bromo-4-(isocyanatomethyl)benzene [ No CAS ]
1-(4-bromo-benzyl)-3-(1H-indol-7-yl)-urea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4740 - 4749

5
[ 5192-04-1 ]
[ 124-63-0 ]
[ 16148-49-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine; In dichloromethane; for 12h;	Utilizing 7-nitro indole and the procedures as described in Scheme VII: Utilizing the aniline intermediate from preparation 8 the title product was prepared by stirring this aniline with pyridine (LEQ) and methansulfonyl chloride (LEQ) in dichloromethane for 12 hrs. After this time the reaction is washed with 1N HC1 and water before being dried over magnesium sulfate and evaporated. This residue is then RECRYSTALIZED from isopropanol to provide the title product as a purple solid (94%). MS (ES+) 210 (M), MS (ES-) 209 (M-1). LC/MS shows 95% purity.
94%	With pyridine; In dichloromethane; for 12h;	N- (lH-Indol-7-yl)-methanesulfonamide Stir lH-indol-7-ylamine with pyridine (1 equivalent) and methanesulfonyl chloride (1 equivalent) in dichloromethane for 12 hrs. Wash the reaction with 1N hydrochloric acid and water, dry over magnesium sulfate, and evaporate. Recrystallize the residue from isopropanol to obtain the title product as a purple solid (94%). MS (ES+) 210 (M), MS (ES-) 209 (M-1). LC/MS shows 95% purity.
82%	With pyridine; In dichloromethane; at 20℃; for 72h;	4.34 g (32.8 mmol) of <strong>[5192-04-1]7-amino-1H-indole</strong> were initially charged in 120 ml of dichloromethane, 3.76 g (32.8 mmol) of methanesulfonyl chloride and 2.60 g (32.8 mmol) of pyridine were added, and the mixture was stirred at RT for three days. After concentrating to one third of the volume, ethyl acetate was added and the mixture was washed successively with 1 M hydrochloric acid, water and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of flash chromatography (eluent: toluene/ethyl acetate 9:1) to obtain 5.63 g (82% of theory) of the title compound.1H-NMR (400 MHz, DMSO-d6): delta=2.97 (s, 3H), 6.46 (t, 1H), 6.98 (t, 1H), 7.06 (d, 1H), 7.36 (t, 1H), 7.41 (d, 1H), 9.31 (s, 1H), 10.8 (s, 1H).LC-MS (method 8): Rt=0.81 min; MS (ESIpos): m/z=211 [M+H]+.

Reference： [1]Patent: WO2004/67529,2004,A1 .Location in patent: Page 75
[2]Patent: WO2005/92854,2005,A1 .Location in patent: Page/Page column 54
[3]Patent: US2011/183928,2011,A1 .Location in patent: Page/Page column 15
[4]Journal of Medicinal Chemistry,2007,vol. 50,p. 6443 - 6445

6
[ 5192-04-1 ]
[ 501-53-1 ]
[ 737801-80-8 ]

Yield	Reaction Conditions	Operation in experiment
96.7%	With sodium hydroxide; In dichloromethane; water; at 10℃; for 2h;Product distribution / selectivity;	(1H-Indol-7-yl)-carbamic acid benzyl ester Equip a 12-L reaction flask with a cooling bath, air driven stirring apparatus, addition funnel, and thermometer probe. Thoroughly purge the flask with nitrogen, charge 7- aminoindole (352 g, 2.663 moles), CH2C12 (5.30 L, 15 volumes) and 2N NaOH (1. 76 L, 3.515 moles). After cooling the biphasic solution to less than 10 C, benzyl chloroformate (500 g, 2.929 moles) add dropwise at such a rate so as to maintain the temperature at less than 10 C over one hour. Stir the reaction vigorously for 1 hour until complete by TLC. Separate the layers and extract the aqueous layer with CH2C12 (1.7 L).
95%		Utilizing the procedures of Scheme XXII, Step A: Indole aniline (800 mg, 6.05 mmol) is dissolved in water (7. 5 ML) and methanol (7.5 mL). The resulting solution is cooled to 0 C IN A SALTWATER/ICE BATH. Sodium carbonate (1.28 g, 12.1 mmol) is added and the resulting slurry stirred for 5 minutes. Benzyl chloro formate (1.04 mL, 7.26 mmol) is added and the reaction stirred at 0 C for 30 minutes. The reaction mixture is then concentrated on the buchi to remove the methanol. The aqueous layer is extracted with CH2C12 (2 X 15 mL). The combined organics are dried (MGS04), filtered and concentrated to provide the intermediate as a purple solid (II) (1. 53 G, 5. 75 mmol, 95%) : 'H NMR (DMSO-D6) 8 10. 8 (broad s, 1 H), 9.4 (broad s, 1 H), 6.9-7. 5 (M, 8 H), 6.9 (t, 1 H, J = 7.8 Hz), 6.4 (q, 1 H, J= 1. 8 Hz), 5.2 (s, 2 H); mass spectrum (M + 1) : 267.2 found.

Reference： [1]Patent: WO2005/92854,2005,A1 .Location in patent: Page/Page column 57
[2]Patent: WO2004/67529,2004,A1 .Location in patent: Page 136 - 137
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 6443 - 6445

7
[ 5192-04-1 ]
[ 1005389-26-3 ]
1H-pyrrole-2,5-dicarboxylic acid bis[(1H-indol-7-yl)-amide] [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 568 - 574

8
[ 1005389-27-4 ]
[ 5192-04-1 ]
azulene-1,3-dicarboxylic acid bis[(1H-indol-7-yl)-amide] [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 568 - 574

9
[ 3739-94-4 ]
[ 5192-04-1 ]
pyridine-2,6-dicarboxylic acid bis[(1H-indol-7-yl)-amide] [ No CAS ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 568 - 574

10
[ 51417-51-7 ]
[ 5192-04-1 ]

Yield	Reaction Conditions	Operation in experiment
		(3) 7-amino-1H-indole; [Show Image] 2.5M n-butyllithium in hexane 16.5 ml (41.3 mmol) was dropped into 50 ml of a solution of 2.70 g (13.8 mmol) of the above compound (2) in tetrahydrofuran at -70C in a nitrogen atmosphere. The mixture was stirred at -70C for 15 minutes and then at -20C to -10C for 30 minutes. The mixture was cooled to -70C again, followed by the dropwise addition of 3.9 ml (18 mmol) of diphenylphosphoryl azide. The resulting mixture was stirred at -70C for 1 hour and at -40C for 1 hour. 3.4M sodium bis(2-methoxyethoxy)aluminum hydride in toluene 22.3 ml (75.8 mmol) was added to the mixture at -40C. The obtained mixture was stirred at -30C to -20C for 30 minutes and then at room temperature for 30 minutes, followed by the addition of a phosphate buffer of pH 7.0. The resulting mixture was filtered to remove insolubles and the filtrate was extracted with ethyl ether. An organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride - successively, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give 1.29 g of the title compound. 1H-NMR(DMSO-d6).delta(ppm):5.01(2H,brs),6.25- 6.33(2H,m),6.70(1H,dd,J=7.9,7.3Hz),6.78(1H,dd,J=7.9,0.7 Hz),7.23(1H,t,J=2.7Hz),10.48-10.72(1H,brm)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226
[2]Patent: EP1813602,2007,A1 .Location in patent: Page/Page column 6-7

11
[ 577-19-5 ]
[ 5192-04-1 ]