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Chemistry
Heterocyclic Building Blocks
Indoles
2-(2-Methyl-1H-indol-1-yl)ethanamine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Indoles
Amines

[ CAS No. 883535-89-5 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 883535-89-5
Chemical Structure| 883535-89-5
Structure of 883535-89-5 *Storage: {[proInfo.prStorage]}

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Quality Control of [ 883535-89-5 ]

COA NMR CNMR HPLC LC-MS

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SDS

Product Details of [ 883535-89-5 ]

CAS No. :883535-89-5MDL No. :MFCD04440779
Formula : C11H14N2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :174.24Pubchem ID :2049534
Synonyms :

Computed Properties of [ 883535-89-5 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 883535-89-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P301 P312-P302 P352-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 883535-89-5 ]

  • Downstream synthetic route of [ 883535-89-5 ]

[ 883535-89-5 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 95-20-5 ]
  • 2-chloroethylamine hydrochloride [ No CAS ]
  • [ 883535-89-5 ]
YieldReaction ConditionsOperation in experiment
99% With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In toluene; for 17.0h;Reflux; Inert atmosphere; To a solution of 2-methylindole (10.04 g, 75 mmol) in toluene (200 mL) are added 2-chloroethylamine hydrochloride (17.4 g, 150 mmol), freshly powdered NaOH (21.00 g, 525 mmol) and tetrabutyl ammonium hydrogen sulfate (2.037 g, 6 mmol). The resulting mixture is heated up to reflux and stirredfor 17h. It is then cooled down to RT, and filtered through a filter paper. The residue is triturated twice with toluene, and filtrated. The filtrate is concentrated under reduced pressure, and the residue is purified by FC, using a gradient of DCM/MeOH from 100:0 to 95:5. After concentration of the product containing fractions, the title compound (13.2 g, 99%) is obtained as a yellow resin: LC-MS A: tR = 0.54 mm; [M+H] = 175.31.
Reference： [1]Patent: WO2018/210995,2018,A1.Location in patent: Page/Page column 20; 23
  • 2
  • [ 883535-89-5 ]
  • 4-{6-[2-(2-methyl-indol-1-yl)ethylamino]pyrimidin-4-yl}benzoic acid [ No CAS ]
Reference： [1]Patent: WO2018/210995,2018,A1
  • 3
  • [ 95-20-5 ]
  • [ 870-24-6 ]
  • [ 883535-89-5 ]
YieldReaction ConditionsOperation in experiment
99% With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In toluene; for 17.0h;Reflux; Inert atmosphere; To a solution of 2-methylindole (10.04 g, 75 mmol) in toluene (200 mL) are added 2-chloroethylamine hydrochloride (17.4 g, 150 mmol), freshly powdered NaOH (21.00 g, 525 mmol) and tetrabutyl ammonium hydrogen sulfate (2.037 g, 6 mmol). The resulting mixture is heated up to reflux and stirred for 17h. It is then cooled down to RT, and filtered through a filter paper. The residue is triturated twice with toluene, and filtrated. The filtrate is concentrated under reduced pressure, and the residue is purified by FC, using a gradient of DCM/MeOH from 100:0 to 95:5. After concentration of the product containing fractions, the title compound (13.2 g, 99%) is obtained as a yellow resin: LC-MS A: tR = 0.54 min; [M+H]+ = 175.31.
Reference： [1]Patent: WO2017/85198,2017,A1.Location in patent: Page/Page column 120
  • 4
  • [ 883535-89-5 ]
  • 5-(6-((2-(2-methyl-1H-indol-1-yl)ethyl)amino)pyrimidin-4-yl)thiophene-2-carbonitrile [ No CAS ]
Reference： [1]Patent: WO2017/85198,2017,A1
  • 5
  • [ 883535-89-5 ]
  • 2-methoxy-4-(6-((2-(2-methyl-1H-indol-1-yl)ethyl)amino)pyrimidin-4-yl)benzonitrile [ No CAS ]
Reference： [1]Patent: WO2017/85198,2017,A1
  • 6
  • [ 883535-89-5 ]
  • [2-(2-methylindol-1-yl)ethyl]{6-[5-(1H-tetrazol-5-yl)thiophen-2-yl]pyrimidin-4-yl}amine [ No CAS ]
Reference： [1]Patent: WO2017/85198,2017,A1
  • 7
  • [ 883535-89-5 ]
  • 5-{6-[2-(2-methylindol-1-yl)ethylamino]pyrimidin-4-yl}-2-(1H-tetrazol-5-yl)phenol [ No CAS ]
Reference： [1]Patent: WO2017/85198,2017,A1
  • 8
  • [ 1193-21-1 ]
  • [ 883535-89-5 ]
  • 6-chloro-N-(2-(2-methyl-1H-indol-1-yl)ethyl)pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine; In isopropyl alcohol; for 2.0h;Reflux; Inert atmosphere; To a solution of 4,6-dichloropyrimidine (3.00 g, 20.1 mmol) in 2-propanol (50 mL) at RT is added 2-(2-methyl-1 H- indol-1-yl)ethan-1-amine (3.68 g, 21.1 mmol) and TEA (3.08 mL, 22.2 mmol). The resulting mixture is refluxed for 2h, then allowed to cool to RT and concentrated under reduced pressure. The residue is partitioned between sat. aq. NaHC03 solution and EtOAc. The layers are separated and the aqueous layer is extracted once more with EtOAc. The combined organic layers are washed with water, brine, dried over MgS04, filtered and the solvent is removed in vacuo yielding the desired product as a yellow powder (5.45 g, 94%). LC-MS A: t = 0.87 min; [M+H]+ = 287.13.
94% With triethylamine; In isopropyl alcohol; for 2.0h;Reflux; Inert atmosphere; To a solution of 4,6-dichloropyrimidine (3.00 g, 20.1 mmol) in 2-propanol (50 mL) at RT is added <strong>[883535-89-5]2-(2-methyl-1H-indol-1-yl)ethan-1-amine</strong> (3.68 g, 21.1 mmol) and TEA (3.08 mL, 22.2 mmol). The resulting mixture is refluxed for2h, then allowed to cool to RT and concentrated under reduced pressure. The residue is partitioned between sat. aq. NaHCO3 solution and EtOAc. The layers are separated and the aqueous layer is extracted once more with EtOAc. The combined organic layers are washed with water, brine, dried over MgSO4, filtered and the solvent is removed in vacuo yielding the desired product as a yellow powder (5.45 g, 94%). LC-MS A: tR = 0.87 mm; [M+H]=287.13.
Reference： [1]Patent: WO2017/85198,2017,A1.Location in patent: Page/Page column 119
[2]Patent: WO2018/210995,2018,A1.Location in patent: Page/Page column 20; 23
  • 9
  • [ 22090-24-0 ]
  • [ 883535-89-5 ]
  • [ 1616960-78-1 ]
YieldReaction ConditionsOperation in experiment
74% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6.0h; 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.
74% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 6.0h; N-(2-(2-Methyl-lH-indol-l-yl)ethyl)-4-(piperidin-l-yl)benzamide (7k) (TG7-152) (Typical procedure): A solution of 2-(2-methyl-lH-indol-l-yl)ethanamine (4a) (65 mg, 0.373 mmol) and 4-(piperidin-l-yl)benzoic acid (5) (76 mg, 1 eq.), and dimethylaminopyridine (catalytic, ~5 mg) in dichloromethane (6 mL) was added l-ethyl-3-(3-dimethylaminopropyl)- carbodiimide.hydrochloride (EDCI) (92 mg, 1.3 eq.) at room temperature. The resulting reaction mixture was stirred for 6 h. At the conclusion of the reaction (TLC), water (15 mL) was added to quench the reaction. The product was extracted with ethyl acetate (20 mL x 3). Organics were washed with dilute HC1 (10 mL), saturated NaHC03 solution (10 ml), water (10 ml) and brine solution (10 ml) and dried over Na2S04 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) (100 mg, 74% yield). 1H NMR (CDC13): delta 7.52 (d, J = 5.6 Hz, 1H), 7.49 (d, J = 8.8 Hz, 2H), 7.30 (d, J = 8 Hz, 1H), 7.07 (m, 2H), 6.80 (m, 2H), 6.23 (s, 1H), 5.98 (t, J = 5.4 Hz, 1H), 4.33 (t, J = 6 Hz, 2H), 3.76 (q, J = 6 Hz, 2H), 3.25 (t, J = 4.8 Hz, 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 C23H27N30: C, 76.42; H, 7.53; N, 11.62; found; C, 75.55; H, 7.50; N, 11.26.
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 88-89
  • 10
  • [ 883535-89-5 ]
  • [ 149-87-1 ]
  • N-(2-(2-methyl-1H-indol-1-yl)ethyl)-5-oxopyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation 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.
Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 82,p. 521 - 535

Tags: 883535-89-5 synthesis path| 883535-89-5 SDS| 883535-89-5 COA| 883535-89-5 purity| 883535-89-5 application| 883535-89-5 NMR| 883535-89-5 COA| 883535-89-5 structure

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