Name: 883535-89-5|2-(2-Methyl-1H-indol-1-yl)ethanamine|95%
Brand: Ambeed
SKU: A710160
Rating: 99 (25 reviews)

1
[ 250683-76-2 ]
[ 883535-89-5 ]
[ 1416881-57-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3.0h;	A solution of 3-fluoro-4-(4-methylpiperazin- l -yl)benzoic acid (75 mg, 0.31 mmol,1 eq.), dimethylaminopyridine (DMAP) (5 mg) in dichloromethane (6 ml) was added to a solution of 2-(2-methyl-l H-indol-l -yl)ethanamine (55 mg, 0.31 mmol, 1 eq.) in dichloromethane (2 ml), followed by l-ethyl-3-(3- dimethylaminopropyl)carbodiimide.hydrochloride (EDCI) (78 mg, 1.13 eq.) at room temperature. The resulting solution was stirred for 3 h. At the conclusion of the reaction (monitored by thin-layer chromatography), water (25 ml) was added to quench the reaction. The organics were separated from aqueous by extraction with ethyl acetate (3 x 20 ml). Combined organics were washed with saturated NaHCCb solution (10 ml), water (10 ml) and brine solution (10 ml). Organics were dried and concentrated to dryness. The resulting crude product was on silica gel chromatography with hexane-ethyl acetate mixture to furnish compound TG7-141 (100 mg, 80% yield). Other compounds were similarly synthesized using appropriate starting materials. TG7- 141 : NMR. delta 7.49 (dd, J = 7.2, 1.2 Hz, 1 H), 7.33 (m, 3H), 7.07 (m, 2H), 6.81 (t, J = 8.4 Hz, 1 H), 6.24 (m, 1 H), 6.23 (s, 1 H), 4.29 (t, J = 5.6 Hz, 2H), 3.70 (q, J = 6.4 Hz, 2H), 3.15 (broad t, J = 4.4 Hz, 4H), 2.55 (t, J = 4.8 Hz, 4H) 2.35 (s, 3H). LCMS calcd for C23H28FN40 (M+H) 395, found: 395
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6.0h;	General procedure: A solution of <strong>[883535-89-5]2-(2-methyl-1H-indol-1-yl)ethanamine</strong> (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL×3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.

Reference： [1]Patent: WO2012/177618,2012,A1 .Location in patent: Page/Page column 51-52
[2]European Journal of Medicinal Chemistry,2014,vol. 82,p. 521 - 535

2
[ 20329-98-0 ]
[ 883535-89-5 ]
[ 1164462-05-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3.0h;	A solution of (E)-3-(3,4,5-trimethoxyphenyl) acrylic acid [220 mg, 0.92 mmol, 1.05 equivalent (eq.)] and dimethylaminopyridine (DMAP) (10 mg) in dichloromethane (6 mL) was added to a solution of 2-(2-methyl- l H- indol- l -yl)ethanamine (152 mg, 0.87 mmol, 1 eq.) in dichloromethane (2 mL), followed by l -ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCI) (190 mg, 1 mmol, 1.13 eq.) at room temperature. The resulting solution was stirred for 3 h. At the conclusion of the reaction (monitored by TLC), water (25 mL) was added to quench the reaction. The organics were separated from aqueous phase by extraction with ethyl acetate (3 x 20 mL). Combined organics were washed with 1% HC1 (10 mL), saturated NaHCC solution (10 mL), water (10 mL), and brine solution (10 mL). Organics were dried and concentrated to dryness. The resulting crude product was recrystallized with hexane-ethyl acetate mixture to furnish pure compound product TG4-155 (300 mg, 85% yield). Proton NMR spectra were recorded in solvent deuteriochloroform (CDCI3) on a Varian Inova-400 (400 MHz), unless otherwise mentioned.TG4- 155: NMR. delta 7.51 (d, J = 6.8 Hz, 1 H), 7.48 (d, J =15.6 Hz, 1 H), 7.29 (d, J= 8 Hz, 1 H), 7.10 (m, 2H), 6.66 (s, 2H), 6.24 (s, 1 H), 6.14 (d, J = 15.6 Hz, 1 H), 5.6 (t, J = 6 Hz, 2H), 4.3 (t, J = 6 Hz, 2H), 3.84 (s, 9H), 3.71 (q, J = 6 Hz, 2H), 2.39 (s, 3H). Anal. Calcd for C23H26N204: C, 70.03; H, 6.64; N, 7.10. Found: C, 69.61 ; H, 6.61 ; N, 7.04.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;	General procedure: Synthesis and structure activity relationship of 1 -indole cinnamic amide analog Indole-2 compounds were prepared as shown wherein step a is NaH, bromoacetonitrile, DMF, 75%; b is Lithium aluminum hydride (LAH), tetrahydrofuran (THF), 32-57%; c is Cinnamic acid derivative (14), l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCI), dimethylaminopyridine (DMAP), CH2C12, 75-80%). The compound 15a possess sites for structural modification, i) Trimethoxyphenyl group, ii) acryl amide moiety iii) ethylene linker, iv) a methyl group on the indole ring.

Reference： [1]Patent: WO2012/177618,2012,A1 .Location in patent: Page/Page column 49
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184
[3]Patent: WO2015/167825,2015,A1 .Location in patent: Page/Page column 92

3
[ 943-89-5 ]
[ 883535-89-5 ]
[ 1415604-20-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

4
[ 25173-72-2 ]
[ 883535-89-5 ]
[ 1415602-43-5 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

5
[ 34841-00-4 ]
[ 883535-89-5 ]
[ 1609030-81-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

6
[ 883535-89-5 ]
[ 951-82-6 ]
N-(2-(2-methyl-1H-indol-1-yl)ethyl)-2-(3,4,5-trimethoxyphenyl)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

7
[ 883535-89-5 ]
[ 60345-99-5 ]
[ 1609030-91-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

8
[ 883535-89-5 ]
[ 191917-03-0 ]
[ 1609030-93-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

9
(2E)-3-[4-(2-hydroxyethoxy)-3,5-dimethoxyphenyl]prop-2-enoic acid [ No CAS ]
[ 883535-89-5 ]
[ 1609030-95-6 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

10
2-(4-fluorophenyl)cyclopropanecarboxylic acid [ No CAS ]
[ 883535-89-5 ]
[ 1609030-98-9 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

11
[ 883535-89-5 ]
[ 1609031-15-3 ]
[ 1609030-85-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

12
[ 220914-34-1 ]
[ 883535-89-5 ]
[ 1609031-01-7 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

13
[ 883535-89-5 ]
(E)-4-[2-(dimethylamino)ethoxy]cinnamic acid [ No CAS ]
[ 1609031-02-8 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

14
[ 883535-89-5 ]
[ 1609031-16-4 ]
[ 1609031-00-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;	General procedure: Compounds 16k-m containing a 2-dimethylaminoethoxyether group were synthesized on the phenyl ring as shown wherein step a is MeOH, H2SO4 (drops), reflux, quantitative; b is Dimethylaminoethanol, PPh3, DIAD, THF, 70%; c is IN NaOH, THF, reflux, quantitative (reagent grade salt); and d is 13a, EDCI, DMAP, DMF, 70%

Reference： [1]Patent: WO2015/167825,2015,A1 .Location in patent: Page/Page column 96
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

15
[ 883535-89-5 ]
[ 20767-04-8 ]
[ 1416881-62-3 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

16
[ 883535-89-5 ]
[ 1429551-15-4 ]
[ 1416881-61-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184

17
[ 104894-21-5 ]
[ 883535-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran;	General procedure: Synthesis and structure activity relationship of 1 -indole cinnamic amide analog Indole-2 compounds were prepared as shown wherein step a is NaH, bromoacetonitrile, DMF, 75%; b is Lithium aluminum hydride (LAH), tetrahydrofuran (THF), 32-57%; c is Cinnamic acid derivative (14), l-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCI), dimethylaminopyridine (DMAP), CH2C12, 75-80%). The compound 15a possess sites for structural modification, i) Trimethoxyphenyl group, ii) acryl amide moiety iii) ethylene linker, iv) a methyl group on the indole ring.

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184
[2]Patent: WO2015/167825,2015,A1 .Location in patent: Page/Page column 92

18
[ 95-20-5 ]
[ 883535-89-5 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4173 - 4184
[2]Patent: WO2015/167825,2015,A1

19
[ 883535-89-5 ]
[ 118-41-2 ]
3,4,5-trimethoxy-N-(2-(2-methyl-1H-indol-1-yl)ethyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6.0h;	General procedure: A solution of <strong>[883535-89-5]2-(2-methyl-1H-indol-1-yl)ethanamine</strong> (4a) (65 mg, 0.373 mmol) and 4-(piperidin-1-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ?5 mg) in dichloromethane (6 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20mL×3). Organics were washed with dilute HCl (10 mL), saturated NaHCO3 solution (10 mL), water (10 mL) and brine solution (10 mL) and dried over Na2SO4 and concentrated. The resulting crude product was subjected to silica gel chromatography eluting with 0-40% ethyl acetate in hexane to furnish 7k (TG7-152) (100mg, 74% yield). 1H NMR (CDCl3): delta 7.52 (d, J=5.6Hz, 1H), 7.49 (d, J=8.8Hz, 2H), 7.30 (d, J=8Hz, 1H), 7.07 (m, 2H), 6.80 (d, J=8.2Hz, 2H), 6.23 (s, 1H), 5.98 (t, J=5.4Hz, 1H), 4.33 (t, J=6Hz, 2H), 3.76 (q, J=6Hz, 2H), 3.25 (t, J=4.8Hz, 4H), 2.37 (s, 3H), 1.6 (m, 6H). LCMS (ESI): >97% purity at lambda 254, MS; m/z, 362 [M+H]+. Anal. Calcd. for C23H27N3O: C, 76.42; H, 7.53; N, 11.62; found; C, 76.48; H, 7.55; N, 11.59.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;	General procedure: Amide derivatives 6a and 6b were synthesized as starting from 2-(2-methyl-lH-indol-l- yl)ethan- 1 -amine (4a) and 3,4,5-trimethoxybenzoic acid (5a) and 3, 4-dimethoxy benzoic acid (5b). The other substituted derivatives on the phenyl ring (6c-z, 7a-z, & 8a-u), isomeric 3-inodole derivatives ((8x-z, & 9a-g),and imidazole derivatives ((8v-w) were synthesized analogous to 6a and 6b as illustrated.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 521 - 535
[2]Patent: WO2015/167825,2015,A1 .Location in patent: Page/Page column 81

20
[ 883535-89-5 ]
[ 93-07-2 ]
[ 689264-90-2 ]