Structure of 1-quinolin-2-ylmethanamine
CAS No.: 5760-20-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 5760-20-3 |
Formula : | C10H10N2 |
M.W : | 158.20 |
SMILES Code : | C1=C2C(=NC(=C1)CN)C=CC=C2 |
MDL No. : | MFCD09261030 |
InChI Key : | HGHPGHVNTQSTNM-UHFFFAOYSA-N |
Pubchem ID : | 3014378 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide;palladium; In water; acetic acid; | a. Imidazo[1,5-a]quinoline A solution of 7.7 g. of 2-cyanoquinoline in 100 ml. of acetic acid is treated with 500 mg. of 5% palladium-on-carbon, and the resulting mixture shaken in a hydrogen atmosphere at room temperature at an initial pressure of 50 psi. When the theoretical amount of hydrogen had been taken up, the catalyst is filtered and the filtrate concentrated in vacuo to a brown oil. Water is added to the residue and rendered basic by the addition of 1N aqueous sodium hydroxide. The product, 2-aminomethylquinoline, is extracted into benzene. The benzene extracts are combined, dried and concentrated to an oil, which is used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | General procedure: In an autoclave, 3.40 g of 6-cyano-3,4-dimethylpyridine (25.7 mmol), 0.15 g of Pd/C (water-content=50%), 200 mL methanol and 3.0 mL concentrated hydrochloric acid are placed, stirred at room temperature for 3 hours while pressurizing with hydrogen to 3 atm. The reaction solution was filtered through Celite and the filtrate was concentrated to dryness. This was washed with methanol to give 2.41 g of 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA) hydrochloride (93% yield). This 2-aminomethyl-3,4-dimethylpyridine hydrochloride was treated with an aqueous solution of potassium carbonate to give 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA) quantitatively. | |
With hydrogenchloride; palladium on activated charcoal; hydrogen; In methanol; water; at 20℃; under 2280.15 Torr; for 3h;Autoclave; | General procedure: In an autoclave, 3.40 g (25.7 mmol) of 6-cyano-3,4-dimethylpyridine, 0.15 g of Pd / C (50% hydrous), 200 mL of methanol and 3.0 mL of concentrated hydrochloric acid are added.The hydrogen was stirred at room temperature under pressure of 3 atm for 3 hours.The reaction solution was filtered through celite, and the filtrate was concentrated to dryness.This was washed with methanol to give 2.41 g (93% yield) of 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2 PICA) hydrochloride.This (2-aminomethyl-3,4-dimethylpyridine hydrochloride was treated with aqueous potassium carbonate solution to quantitatively obtain 2-aminomethyl-3,4-dimethylpyridine (3,4-Me2PICA). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,2-dimethoxyethane; | 6-Amino-2-furan-2-yl-4-[(quinolin-2-ylmethyl)-amino]-nicotinonitrile From trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester and <strong>[5760-20-3]2-(aminomethyl)quinoline</strong> in DME. ES-MS m/e (%): 342 (M+H+, 100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
palladium; In water; acetic acid; | a. Imidazo[1,5-a]quinoline A solution of 7.7 g. of 2-cyanoquinoline in 100 ml. of acetic acid is treated with 500 mg. of 5% palladium-on-carbon, and the resulting mixture shaken in a hydrogen atmosphere at room temperature at an initial pressure of 50 psi. When the theoretical amount of hydrogen had been taken up, the catalyst is filtered and the filtrate concentrated in vacuo to a brown oil. Water is added to the residue and rendered basic by the addition of 1N aqueous hydroxide. The product, 2-aminomethylquinoline, is extracted into benzene. The benzene extracts are combined, dried and concentrated to an oil, which is used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; | Following the procedure of Preparation AIII-a, 7.92 g. of <strong>[5760-20-3]2-aminomethylquinoline</strong> is formylated with 50 ml. of 97% formic acid to give 5.97 g. of 2-formamidomethylquinoline, m.p. 108-114 C. | |
With formic acid; | Following the procedure of Preparation AIII-a, 7.92 g. of <strong>[5760-20-3]2-aminomethylquinoline</strong> is formylated with 50 ml. of 97% formic acid to give 5/97 g. of 2-formamidomethylquinoline, m.p. 108-114 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | EXAMPLE 9 Reduction of 2-Cyanoquinoline Using the method of Example 1 gave an 88% yield of 2-quinolinemethanamine by spectroscopic analysis at 4F/mole. Increasing charge passed decreased the yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With triethylamine; In ethanol; at 20℃; for 22h; | General procedure: To a solution of [(1S,2R)-3-[[[3-[(dimethylamino)methylene]-2,3-dihydro-2-oxo-1H- indol-5-yl]sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid, (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ester 8 (32 mg, 0.050 mmol) in absolute ethanol (1 ml) was added neopentylamine (29 mul, 0.25 mmol). The resulting solution was stirred 22 h and then concentrated in vacuo. The residue was purified on a preparative TLC plate (20 x 20 cm, 500 mum) using 8:2 EtOAc/hexane as eluant to provide [1-benzyl-3-({3-[(2,2-dimethyl-propylamino)-methylene]-2-oxo- 2,3-dihydro- 1H-indole-5-sulfonyl}-isobutyl-amino)-2-hydroxy-propyl]-carbamic acid hexahydro- furo[2,3-b]furan-3-yl ester 9n (24 mg, 70%). MS m/z 685.3 (MH)+, 1H NMR (CDCl3) 9.15 (m, 1H), 8.70 (s, 1H), 7.66 (s, 1H), 7.61 (d, J = 13.2, 1H),7.43 (dd, J = 8.4, 2.0, 1H), 7.24 (m, 5H), 7.00 (d, J = 8.0, 1H), 5.64 (d, J = 5.2, 1H), 5.11 (d, J = 8.4, 1H), 5.00 (m, 1H), 3.65 - 3.93 (m, 7H), 3.18 (d, J = 6.8, 2H), 2.75 - 3.22 (m, 7H), 1.83 (m, 1H), 1.60 (m, 1H), 1.42 (m, 1H), 1.01 (s, 9H), 0.84 - 0.95 (m, 6H). |
A650215 [18004-62-1]
Quinolin-2-ylmethanamine dihydrochloride
Reason: Free-salt