| 100% |
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 760.051 Torr; for 2.5h; |
The mixture of Ib (300mg, 1.36mmol) and Pd/C (10%, 300mg) in methanol was hydro genated at atmosphere at r.t. for 2.5h, filtered and concentrated to give Ic (258mg, 100%). |
| 99% |
With hydrogen; palladium; In tetrahydrofuran; at 20℃; |
To a solution of 4-(5-nitropyridin-2-yl) morpholine (3.89 g, 18.60 mmol) in THE (100 mL) was added catalyst Pd/C (0.5 g). The reaction was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo to give the title compound as a brown-red solid (3.30 g, 99%). |
| 99% |
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 20℃; |
To a solution of 4-(5-nitropyridin-2-yl)morpholine (3.89 g, 18.60 mmol) in THF (100 mL) was added catalyst Pd/C (0.5 g). The reaction was stirred at rt under H2 overnight, and filtered. The filtrate was concentrated in vacuo to give the title compound as a brown-red solid (3.30 g, 99%). |
| 99% |
With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 20℃; |
In a 100 mL round bottom flask, 4-(5-nitropyridin-2-yl)morpholine (3.89 g, 18.60 mmol) was dissolved in THF (100 mL),After palladium/carbon (0.5 g) was added, H2 was bubbled in and stirred overnight at room temperature.After the mixture was filtered, the filtrate was collected and the solvent was evaporated under reduced pressure and dried in vacuo to give a red-brown solid (3.30 g, 99%). |
| 97% |
With palladium 10% on activated carbon; hydrogen; In ethanol; ethyl acetate; at 70℃; under 750.075 Torr; for 0.5h;H-Cube; |
(General flow chemistry reduction method). Using 10% Pd/C as catalyst, a solution of compound 3b (1 mmol, 208 mg) in a 1:1 mixture of ethyl acetate: ethanol (30 mL) was pumped though the H-Cube. The pressure of the system was set to 1 bar, and the temperature to 70 C. After 30 minutes, all the reaction mixture had passed though the HCube. The fraction was analyzed using TLC, which showed complete conversion of the product, and the solvent was reduced to dryness, affording a dark red oil 171 mg (96%) yield. The CatCart was then washed with ethanol for approximately 10 minutes and the washings were discarded. |
| 88% |
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2068.65 Torr; for 2h; |
Into a EtOH (250 mL) solution of 4-(5-nitropyridin-2-yl)morpholine (4.9 g, 23.4 mmol), 10% Pd on activated carbon, 500 mg, was added. Hydrogenation was carried out in a Parr flask at room temperature, at 40 psi for 2 hr. The solids were filtered off and the filtrate was collected. The solvent was removed in vacuo. 6-Morpholinopyridin-3-amine, as a purple solid, was obtained: 3.7 g (88% yield); 1H NMR (300 MHz, DMSO) delta 7.64 (d, J=2.7, 1H), 6.96 (dd, J=2.7, 8.8, 1H), 6.65 (d, J=8.8, 1H), 4.63 (s, 2H), 3.72-3.69 (m, 4H), 3.21-3.18 (m, 4H); LCMS (M+) m/z 180.08. |
| 87% |
With palladium 10% on activated carbon; hydrogen; In ethanol; at 25℃; under 760.051 Torr; for 16h; |
Under hydrogen (1 atm), to a solution of compound 62-b (2.0 g, 9.62 mmol) in ethanol (20 mL) was added 10% Pd-C (0.2 g). The mixture was stirred at 25 C. for 16 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give brown solid 62-a (1.5 g, yield: 87%), which was used directly for the next step without purification. LC-MS (ESI): m/z=180 [M+H]+. |
| 85% |
With palladium 10% on activated carbon; hydrogen; for 2h; |
To a solution of the compound ha (2.50g, 11.9Smmol) in MeOH (5OmL) palladium 10% on carbon (0.51 g) was added. The resulting mixture was stirred under hydrogen atmosphere for 2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to afford the compound lib (1.82g, 85%). |
| 84% |
With palladium on activated charcoal; hydrogen; In methanol; at 20℃; under 760.051 Torr; for 3h; |
To a solution of 4-(5-nitropyridin-2-yl)morpholine (210 mg, 1 mmol) in methanol (15 mL) was added Pd/C (20 mg), and the mixture was hydrogenated at r.t under atmosphere pressure for 3 h. TLC showed that the reaction was complete. The resultant was filtered to remove Pd/C, and the filtrate was purified by silica gel column (PE/EtOAc, 1/1) to give 150 mg (yield: 84%) of 6-morpholinopyridin-3-amine as a brown solid |
| 79.3% |
With hydrogenchloride; iron; In ethanol; water; at 80℃; for 3h; |
General procedure: To the solution of 14a-c, 14e-g, 15a-g, 16a-c or 17a-c (0.005mol) in ethanol/water (9:1, 30mL) was added hydrochloric acid (1.0mL) and iron powder (1.12g, 0.02mol). The resulting mixture was heated at 80C for 3h, filtered through celite and concentrated to remove ethanol. The aqueous solution was extracted with ethyl acetate (3×100mL) and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to gain 18a-c, 18e-g, 19a-g, 20a-c or 21a-c |
| 74% |
With palladium on activated charcoal; hydrazine hydrate; In butan-1-ol; at 120℃; for 6h; |
Pd-C (5 mmol) catalyst was added to the solution ofcompound 2 (10 mmol) in butanol, and the mixture wasallowed to reflux in the presence of hydrazine hydrate (50mmol) for 6 hours. The progress of the reaction was monitoredby TLC. After completion of the reaction, the catalyst wasremoved by filtration, and the reaction solvent was removedunder reduced pressure. The obtained white solid wasrecrystallized from ethanol to afford the desired compound |
| 70% |
With palladium on carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr; for 12h; |
General procedure: A mixture of 2-chloro-5-nitropyridine (3) (50mmol), morpholine (100mmol), and K2CO3 (100mmol) in THF (50mL) were stirred at 80C for 4h. And then the mixture was concentrated to 20mL and poured into water (100mL), the yellow solid precipitation formed. After filtration, wash with purified water and dry, the desired compound 3a was obtained. 3b Was got with the same method. The mixture of 3a-3b (20mmol) and Pd/C (20%, 500mg) in methanol was hydrogenated at atmosphere at r.t. for 12h, followed by filtration and concentration to afford compounds 4a-4b. |
|
With hydrogen;palladium on activated charcoal; In methanol; at 20℃; for 4h; |
A mixture of 2-chloro-5-nitropyridine (2 g, 12. 6 mmol) and morpholine (4.4 g, 50.5 mmol) was stirred at a room temperature for 1 hour.. water was added to the reaction mixture and the crystals separated out therefrom were filtered to obtain yellow powdery crystals.. methanol (30 ml) and palladium carbon (0.25 g) were added thereto, the mixture was stirred in a hydrogen atmosphere at a room temperature for 4 hours, insoluble matters were filtered off using Celite and the filtrate was concentrated under a reduced pressure.. To the resulting residue were added methanol (20 ml) and dimethylformamide dimethylacetal (1.81 g, 15.2 mmol), followed by stirring under refluxing for 2 hours.. The reaction mixture was cooled down to room temperature and concentrated under a reduced pressure, and methanol (20 ml) and hydroxylamine hydrochloride (1.05 g, 15.2 mol) were added thereto, followed by stirring at room temperature for 4 hours.. The reaction mixture was concentrated under a reduced pressure and a saturated aqueous solution of sodium hydrogen carbonate (10 ml) was added thereto, followed by extracting with ethyl acetate.. The organic layer was dried over MgSO4, concentrated under a reduced pressure, purified by an NH type silica gel column chromatography (developing solvents; n-hexane: ethyl acetate = 1:1) and recrystallized from ethyl acetate to obtain the title compound (0.985 g) (the compound 127 in Table 1 which will be shown after) in colorless powder. Melting point: 172.0 to 174.0C. |
|
With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 2585.81 Torr; for 3h; |
Preparation of 6-morpholin-4-yl-pyridin-3-ylamine A mixture of 2-chloro-5-nitro-pyridine (5 g, 31 mmol), morpholine (13 mL, 155 mmol), and triethylamine (10 mL) in dichloromethane (30 mL) was stirred at room temperature for 3 hr. After the reaction, the reaction mixture was mixed with water, and two layers were separated. The aqueous layer was extracted with CH2Cl2 two times. Organic layers were collected, combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to give 4-(5-nitro-pyridin-2-yl)-morpholine (6.48 gm, 100%) as a yellow solid. LCMS calcd for C9H11N3O3 (m/e) 209, obsd 210 (M+H). The solution of 4-(5-nitro-pyridin-2-yl)-morpholine (1.5 g, 7.18 mmol) in ethyl acetate (20 mL) in the presence of 10% palladium on carbon (0.75 g) was shaken under the hydrogen with a pressure of 50 psi at room temperature for 3 hr. After the reaction, the reaction mixture was filtered through a plug of celite and the filtration pad was washed with ethyl acetate. The organic layer was collected, concentrated, and dried to give 6-morpholin-4-yl-pyridin-3-ylamine (1.11 g, crude) as a light red solid, which was directly used in the next step reaction without further purification. LCMS calcd for C9H14N3O (m/e) 179, obsd 180 (M+H). |
|
With iron; acetic acid; at 60℃; for 2h; |
A mixture of compound 41 (4 g, 19.1 mmol) in HOAc (40 ml) was added iron powder (5.34 g, 89.53 mmol). The mixture was heated to 60C and stirred for 2h, then the mixture was filtered through celite, the filted cake was washed with HOAc and then water. The filtrate was concentrated and the residue was neutralized with saturated NaHC03 solution, the aqueous was extracted with EtOAc (100 ml x 5) and DCM (100 ml x 2). The organic combined extracts were washed with brine, dried over NaS04, filtered and concentrated to afford crude compound 42 (2.7 g, yield 79%) as a red solid, used in the next step without further purification. m / z: [M+H] + 180.3 |
|
With iron; acetic acid; at 60℃; for 2h; |
[0320] A mixture of compound 41 (4 g, 19.1 mmol) inHOAc ( 40 ml) was added iron powder (5.34 g, 89.53 mmol).The mixture was heated to 60 C. and stirred for 2 h, then themixture was filtered through celite, the filtered cake waswashed with HOAc and then water. The filtrate was concentratedand the residue was neutralized with saturatedNaHCO solution, the aqueous was extracted with EtOAc(100 ml~5) and DCM (100 mlx2). The organic combinedextracts were washed with brine, dried over NaS04 , filteredand concentrated to afford crude compound 42 (2.7 g, yield79%) as a red solid, used in the next step without furtherpurification.[03211 rnlz: [M+Hr 180.3 |
|
With palladium 10% on activated carbon; hydrogen; In methanol; for 1h;Inert atmosphere; |
Synthesis of compound 184.3. A solution of 184.2 (0.650g, 0.365mmol, l .Oeq) in MeOH (20mL) was added 10% Pd/C (0.200g) under nitrogen. It was purged with H2 for 1 hour. Reaction mixture was filtered through celite and obtained filtrate was concentrated under reduced pressure to get crude 184.3 (0.50 g, 89.8 %) which was used as such for the next step, MS (ES): m/z 179.23 [M+H]+. |
|
With hydrogenchloride; tin(II) chloride dihdyrate; In ethanol; at 80℃; for 8h;Reflux; |
Compound 8a (0.67 g, 3.2 mmol) was dissolved in ethanol solution and heated to reflux at 80C, before stannous chloride dihydrate (2.6 g, 12.8 mmol) were added. 37% hydrochloric acid was added. The mixture was stirred for 8 hours. The solvent was evaporated in vacuum, neutralized to strong alkaline with 1 mol/L sodium hydroxide solution and then extracted with ethyl acetate for two times. The combined organic phase was washed with saturated sodium chloride solution and then dried by sodium sulfate. The mixture was filtered and the filtrate was concentrated in vacuum to give 9a as a black solid. Compound 9b was obtained as the same procedure as 9a |
|
With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 2h; |
General procedure: Nitro-compound (2a-2e) was dissolved in methanol and stirred at room temperature with palladium/charcoal (5mol%) in a hydrogen gas environment for 2h. The resulting solution was filtered through celite, concentrated, and used in the next step without further purification. |
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