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Chemical Structure| 52023-68-4 Chemical Structure| 52023-68-4

Structure of 6-Morpholinopyridin-3-amine
CAS No.: 52023-68-4

Chemical Structure| 52023-68-4

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Product Details of [ 52023-68-4 ]

CAS No. :52023-68-4
Formula : C9H13N3O
M.W : 179.22
SMILES Code : NC1=CC=C(N2CCOCC2)N=C1
MDL No. :MFCD00119562
InChI Key :VVTSPTCBHTWXMD-UHFFFAOYSA-N
Pubchem ID :104059

Safety of [ 52023-68-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 52023-68-4 ]

* 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.

  • Downstream synthetic route of [ 52023-68-4 ]

[ 52023-68-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 853917-64-3 ]
  • [ 52023-68-4 ]
  • [6-(6-morpholino-[3]pyridylamino)-[3]pyridyl]-arsonic acid [ No CAS ]
  • 2
  • [ 26820-62-2 ]
  • [ 52023-68-4 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;platinum on carbon; In ethanol; under 2585.81 Torr; for 5h; A mixture containing 1.65 g (7.8 mmol) of 4-(5-nitro-2-pyridinyl)morpholine, 160 mg of 5 % Pt on carbon, and 20 ml. of EtOH was subjected to a 50 psi H2 atm for 5 h. The reaction mixture was filtered through a pad of Celite and the solvents were removed under reduced pressure to give 1.4 g (100%) of 6-(4-morpholinyl)-3- pyridinamine as a purple solid: 1H NMR (400 MHz, DMSO-c/6) delta 7.60 (d, J = 2.9 Hz, 1 H), 6.92 (dd, J = 8.8 and 2.9 Hz, 1 H), 6.62 (d, J = 8.8 Hz, 1 H), 4.59 (brs, 2 H), 3.65 - 3.72 (m, 4 H), and 3.17 (dt, J = 4.9 and 2.4 Hz, 4 H).
100% With hydrogen;5%-palladium/activated carbon; In ethanol; under 2585.81 Torr; for 5h; Step B: 6-(4-Morpholinyl)-3-pyridinamine; A mixture containing 1.65 g (7.8 mmol) of 4-(5-nitro-2-pyridinyl)morpholine, 160 mg of 5% Pt on carbon, and 20 mLof EtOHI was subjected to a 50 psi H2 atmosphere for 5 h. The reaction mixture was filtered through a pad of Celite and the solvents were removed under reduced pressure to give 1.4 g (100%) of 6-(4-morpholinyl)-3- pyridinamine as a purple solid: 1H-NMR (400 MHz, DMSO-Of6) delta 7.60 (d, J = 2.9 Hz, 1 H), 6.92 (dd, J =8.8 and 2.9 Hz, 1 H), 6.62 (d, J = 8.8 Hz, 1 H), 4.59 (brs, 2 H), 3.65 - 3.72 (m, 4 H), and 3.17 (dt, J =4.9 and 2.4 Hz, 4 H).
100% With hydrogen;platinum on carbon; In ethanol; at 20℃; under 2585.81 Torr; for 5h; A mixture containing 1 65 g (7 8 mmol) of 4-(5-niotatro-2-pyriotadiotanyl)morpholiotane, 160 mg of 5% Pt on carbon, and 20 mL of EtOHI was subjected to a 50 psi H2 atmosphere for 5 h The reaction mixture was filtered through a pad of Celite and the solvents were removed under reduced pressure to give 1 4 g (100%) of 6-(4-morpholiotanyl)-3- pyridinamine as a purple solid 1H-NMR (400 MHz, DMSO-Cf6) delta 7 60 (d, J = 2 9 Hz, 1 H), 6 92 (dd, J =8 8 and 2 9 Hz, 1 H), 6 62 (d, J = 8 8 Hz, 1 H), 4 59 (brs, 2 H), 3 65 - 3 72 (m, 4 H), and 3 17 (dt, J =4 9 and 24 Hz, 4 H)
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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  • 3
  • [ 52023-68-4 ]
  • 4-(5-azidopyridin-2-yl)morpholine [ No CAS ]
  • 4
  • [ 475301-75-8 ]
  • [ 52023-68-4 ]
  • C25H31N5O5S [ No CAS ]
  • 5
  • [ 52023-68-4 ]
  • [ 117-34-0 ]
  • N-(6-morpholin-4-yl-pyridin-3-yl)-2,2-diphenyl-acetamide [ No CAS ]
  • 6
  • [ 638218-95-8 ]
  • [ 52023-68-4 ]
  • 2-methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzofuran-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 20℃; for 17h; A solution of 2-methyl-6-[thieno[3, 2-b] pyridin-7-yloxy] benzofuran-3-carboxylic acid 100 (70mg, 0.215 mmole), 6-Morpholin-4-yl-pyridin-3-ylamine (77 mg, 0.43 mmole), HATU (163 mg, 0.43 mmole), and diisopropylethylamine (75 [PI,] 0.43 [MMOLE)] were stirred in [DMF (] [2ML)] at ambient temperature for 17 hr. The mixture was then added dropwise to a solution of cold aqueous [NAHC03] resulting in a precipitate which was collected by filtration. This material was purified on silica gel using a gradient of 0 to 5% methanol in a 1: 1 mixture of ethyl acetate and [DICHLOROMETHANE] as eluent to give 77 mg (74%) of a lavander [SOLID.'H] NMR (CD3CN) 8 8.50 (1 H, d, J = 5.3 Hz), 8.37 (1 H, d, J = 2.5 Hz), 8.29 (1 H, s), 7.92-7. 88 (3H, m), 7.54 [(1 H.] d, [J=5. 3HZ),] 7.45 (1 H, d, [J=2. 0HZ),] 7.23 [(1 H, DD, J = 8. 6,] 2. 0 Hz), 6.78 (1H, d, [J = 9.] 1 Hz), 6.64 [(1 H,] d, [J = 5. 3 HZ),] 3.76 [(4H,] t, J = 4. 9 Hz), 3.44 (4H, t, [J = 4. 9 HZ),] 2.72 (3H, s). Anal. [CALCD] for [C26H22N404S] : C, 64.18 ; H, 4.56 ; N, 11.52 ; S, 6.59. Found: C, 64.42 ; H, 4.77 ; N, 11.32 ; S, 6.50.
  • 7
  • 3-dimethylaminomethylene-6-(2-furanyl)oxindole (E isomer) [ No CAS ]
  • 3-dimethylaminomethylene-6-(2-furanyl)oxindole [ No CAS ]
  • [ 52023-68-4 ]
  • 6-(2-furyl)-3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 6-(2-furyl)-3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 8
  • [ 297757-16-5 ]
  • [ 52023-68-4 ]
  • ethyl 3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]
  • ethyl 3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 9
  • 3-dimethylaminomethylene-6-phenyloxindole (E isomer) [ No CAS ]
  • 3-dimethylaminomethylene-6-phenyloxindole (Z isomer) [ No CAS ]
  • [ 52023-68-4 ]
  • 3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-6-phenyl-1,3-dihydro-2H-indol-2-one [ No CAS ]
  • 3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-6-phenyl-1,3-dihydro-2H-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 10
  • [ 297757-18-7 ]
  • [ 52023-68-4 ]
  • 3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-5-phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-5-phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells.Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 11
  • [ 295327-31-0 ]
  • [ 52023-68-4 ]
  • 5-(2-furyl)-3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 5-(2-furyl)-3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells.Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 12
  • [ 295327-32-1 ]
  • [ 52023-68-4 ]
  • 3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-5-(3-thienyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-5-(3-thienyl)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells.Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 13
  • [ 295327-33-2 ]
  • [ 52023-68-4 ]
  • 5-bromo-3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 5-bromo-3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 14
  • [ 295327-34-3 ]
  • [ 52023-68-4 ]
  • 6-chloro-3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 6-chloro-3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 15
  • [ 295327-35-4 ]
  • [ 52023-68-4 ]
  • 3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
  • 3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomer 9 and Monomer 10 were generated in situ by preparing stock solutions of the corresponding aza-oxindole. For example, 20.1 mg of 4-aza-oxindole was dissolved in 4.0 mL of ethanol. Both of the precursors for monomers 9 and 10 were transferred (0.20 ml/well) to a 96-well dry heating block (vwrBRAND Dry Block Heater, cat No.13259-066) according to the map below where M represents the monomer and A represents the amine. The ethanol was evaporated off at 50 C. until it was clear that there was no solvent remaining. DMF (0.20 mL) was added followed by the addition of dimethylformamide di-t-butylacetal (0.003 mL) and this remained at room temperature for 1 h. Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 16
  • [ 295327-36-5 ]
  • [ 52023-68-4 ]
  • 3-((E)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one [ No CAS ]
  • 3-((Z)-[6-(4-morpholinyl)-3-pyridinyl]amino}methylidene)-1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); ethanol; at 40 - 70℃; for 20h;Heating / reflux; Monomer 9 and Monomer 10 were generated in situ by preparing stock solutions of the corresponding aza-oxindole. For example, 20.1 mg of 4-aza-oxindole was dissolved in 4.0 mL of ethanol. Both of the precursors for monomers 9 and 10 were transferred (0.20 ml/well) to a 96-well dry heating block (vwrBRAND Dry Block Heater, cat No.13259-066) according to the map below where M represents the monomer and A represents the amine. The ethanol was evaporated off at 50 C. until it was clear that there was no solvent remaining. DMF (0.20 mL) was added followed by the addition of dimethylformamide di-t-butylacetal (0.003 mL) and this remained at room temperature for 1 h. Monomers 1 through 8 (0.20 mL/well) were transferred to the appropriate wells in the dry block heater according to the plate map below. After the in situ conversion of monomer 9 and 10 was complete, the aniline set (0.20 mL/well) was transferred to the appropriate wells according to the plate map below. The plates were heated to 70 C. for 4 h and then the reaction was cooled to 40 C. and heating was continued for another 16 h. Ethanol was added as necessary to keep a constant reaction volume in the wells. Upon completion of the reaction, methanol (1.0 mL) was added to each well. Using a multi-pipettor, the contents of the reaction wells were transferred to the appropriate wells of a 96-well (Beckmann) plate. The volatiles were removed using a nitrogen flow to substantially reduce the volume of solvent, followed by placing the plates in a vacuum drying oven at 70 C. under 15 mmHg of pressure. The average weight of product determined for plate 1 was 1.91 mg/well (70% conversion). The average weight of product determined for plate 2 was 1.78 mg/mL (70% conversion). All of the wells were analysed by LC-MS.
  • 17
  • [ 85196-50-5 ]
  • [ 52023-68-4 ]
  • [ 733039-00-4 ]
YieldReaction ConditionsOperation in experiment
In chloroform; at -10 - 20℃; for 21h; To a stirring solution OF CYCLOPENTYL- (4, 6-DICHLORO- [1, 3,5] triazin-2-yl) - amine (Compound A') (0.105g, 0. 451MMOL) in chloroform (5 mL) at-10 C was added a solution of <strong>[52023-68-4]6-morpholin-4-yl-pyridin-3-ylamine</strong> (0. 081g, 0.451 mmol) in chloroform (3 mL) over 20 minutes. The reaction was allowed to stir at-10 C for 1 hour. The reaction was allowed to warm to ambient temperature and stirred overnight. After stirring for 20 hours, the reaction mixture was diluted with dichloromethane and partitioned with water. The organic phase was washed twice with water and then collected, dried over NASSO., filtered and concentrated under reduced pressure to yield 6-CHLORO-N-CYCLOPENTYL-N'-(6-MORPHOLIN-4-YL-PYRIDIN-3- YL)- [1, 3,5] triazine-2, 4-diamine (Compound E) as a purple foam (0. 103G, 33%). MS 376.1 ; MP 218-219.
  • 18
  • [ 52023-68-4 ]
  • [ 4637-24-5 ]
  • [ 474654-11-0 ]
YieldReaction ConditionsOperation in experiment
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.
YieldReaction ConditionsOperation in experiment
95% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h; General procedure: To a stirring solution of l-methyl-4-(3-nitro-pyridin-2-yl)-piperazine (LXXXIII) (1.30 g, 5.85 mmol) in MeOH (15 mL) was added 10% Pd/C. The solution was purged with hydrogen. The solution was stirred at room temperature for 16 h under hydrogen. The solution was filtered through a pad of Celite and concentrated to a residue under vacuum. The residue was purified by column chromatography (100% CHC13? 2:98 MeOH[7N NH3]:CHC13) to afford 2-(4-methylpiperazin-l-yl)pyridin-3 -amine (LXXXIV) (0.466 g, 2.42 mmol, 52% yield) as a tan solid. ESIMS found for Ci0Hi6N4 mlz 192 A (M+H).
95% With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 6h; General procedure: Step 2 10% Palladium on carbon (40 mg) was added to a solution of 1-methyl-4-(5-nitropyridin-2-yl)piperazine (LIX) (3.80 g, 17.09 mmol) in EtOH (50.0 mL). The flask was evacuated and replaced with a hydrogen atmosphere. The solution was stirred at room temperature for 6 h under hydrogen. The catalyst was filtered through a pad of Celite, and the solvent was removed under reduced pressure to afford 6-(4-methylpiperazin-1-yl)pyridin-3-amine (LX) as a brown viscous oil which solidified under vacuum (3.30 g, 17.1 mmol, quantitative).
95% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h; General procedure: stirring solution of l-methyl-4-(3-nitro-pyridin-2-yl)-piperazine (0543) (LXXXIII) (1.30 g, 5.85 mmol) in MeOH (15 mL) was added 10% Pd/C. The solution was purged with hydrogen. The solution was stirred at room temperature for 16 h under hydrogen. The solution was filtered through a pad of Celite and concentrated to a residue under vacuum. The residue was purified by column chromatography (100% CHC ? 2:98 MeOH[7N NH3]:CHC13) to afford 2-(4-methylpiperazin-l-yl)pyridin-3 -amine (LXXXIV) (0.466 g, 2.42 mmol, 52% yield) as a tan solid. ESIMS found for Ci0Hi6N4 mlz 192 A (M+H).
95% With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 6h; General procedure: 10% Palladium on carbon (40 mg) was added to a solution of 1-methyl-4-(5-nitropyridin-2-yl)piperazine (LXXVIII) (3.80 g, 17.09 mmol) in EtOH (50.0 mL). The flask was evacuated and replaced with a hydrogen atmosphere. The solution was stirred at room temperature for 6 h under hydrogen. The catalyst was filtered through a pad of Celite, and the solvent was removed under reduced pressure to afford 6-(4-methylpiperazin-1-yl)pyridin-3-amine (LXXIX) as a brown viscous oil which solidified under vacuum (3.30 g, 17.1 mmol, quantitative). ESIMS found for C10H16N4 m/z 193.0 (M+H).
C. The following pyrdin-3-ylamines were prepared by the method described above: 6-(piperidin-1-yl)pyridin-3-ylamine; 6-(morpholin-4-yl)pyridin-3-ylamine; 6-(4-methylpiperazin-1-yl)pyridin-3-ylamine; and 6-[di-(2-hydroxyethyl)amino]pyridin-3-ylamine.
With potassium carbonate; In dimethyl sulfoxide; at 190℃; for 10h; General procedure: A mixture of 6-chloropyridin-2-amine (19.3 g, 150 mmol), K2C03 (41.7 g, 0.30 mol) and morpholine (38.9 mL, 450 mmol) in DMSO (150.0 mL) was stirred at 190 C (oil bath) for 10 h. After cooling to room temp, water (300.0 mL) was added and the mixture was extracted with ethyl acetate (4 x 150.0 mL). The combined organic layers were washed with water (3 x 25.0 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by silica gel chromatography (10: 1 petroleum ether : ethyl acetate) to give 6- morpholinopyridin-2-amine as a white solid (9.0 g, 54.8 mmol). MS (ESI) calcd for C9Hi3N30 (m/z): 179.11, found 180 [M+H].
With potassium carbonate; In dimethyl sulfoxide; at 190℃; for 16h;Sealed tube; General procedure: In a sealed flask were solved 10 2-bromopyridin-4-amine (100 mg, 0.58 mmol) and 41 morpholine (0.25 mL, 2.9 mmol) in 0.8 mL of dry 42 DMSO. 43 Potassium carbonate (239.6 mg, 1.73 mmol) was added to the mixture and the reaction was stirred at 190C for 16 hours. The mixture was quenched with 44 NaHCO3 saturated and extracted with ethyl acetate. The organic layer was dried and concentrated. The crude was purified by CombiFlash column chromatography (DCM/MeOH) to afford the desired 45 product (25 mg, 24.1 %). 1H-NMR (400 MHz, DMSO-d6): delta = 7.63 (d, 1 H), 5.98 (dd, 1 H), 5.85 (s, 3H), 3.66 (m, 4H), 3.27 (m, 4H). HPLC-MS: Rt 1.661; m/z 180.0 (MH+).

  • 20
  • 7-fluoro-6-[(7-methoxyquinolin-4-yl)oxy]-2-methyl-1-benzofuran-3-carboxylic acid [ No CAS ]
  • [ 52023-68-4 ]
  • 7-fluoro-6-[(7-methoxyquinolin-4-yl)oxy]-2-methyl-N-(6-morpholin-4-ylpyridin-3-yl)-1-benzofuran-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6-morpholin-4- ylpyridin-3-amine 113-H, which is commercially available from BIONET, was then added according to Scheme IV (iii) to yield the final product 7-fluoro-6- [ (7-methoxyquinolin-4-yl) oxy] -2- methyl-N-(6-morpholin-4-ylpyridin-3-yl)-1-benzofuran-3-carboxamide 113. 1H NMR (DMSO-d3, 400MHz) # : 10.05 (1H, s), 8.56 (1H, d, J = 5.3 Hz), 8.40 (1H, s), 8.22 (1H, d, J = 9. 1 Hz), 7.86 (1H, dd, J = 9. 0,1. 9 Hz), 7.60 (1H, d, J = 8. 6 Hz), 7. 38-7. 34 (2H, m), 7.28 (1H, dd, J = 9.1, 2.5 Hz), 6.83 (1H, d, J = 9.1 Hz), 6.43 (1H, d, J = 5.1 Hz), 3.89 (3H, s), 3.65 (4H, t, J = 5.0 Hz), 3.34 (4H, t, J = 5.0 Hz), 2.66 (3H, s). HRMS (ESI) C29H26FN405 (M + H+) m/z : Calc. 529.1887 ; Found: 529.1888. Anal. (C29H26FN4O5 1. 0 H20) Calc'd : C, 63.73 ; H, 4.98 ; N, 10.25. Found: C, 63.49 ; H, 4.75 ; N, 9.94.
  • 21
  • [ 898270-94-5 ]
  • [ 52023-68-4 ]
  • 2-tert-butyl-4-[(6-morpholin-4-ylpyridin-3-yl)amino]-5-phenylisothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With triethylamine; In acetonitrile; at 140℃; for 1h;Microwave irradaition; Example 4; 2-fc/f-ButyI-4-[(6-morpholin-4-ylpyridin-3-yl)amino]-5-phenylisothiazol-3(2flr)-one 1,1- dioxide; A solution of 2-te/t-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1 -dioxide (0.150g, 0.50mmol), 6-mophiholin-4-ylpyridin-3-amine (0.108g, 0.60mmol) and TEA (0.06mL, 0.60mmol) in MeCN (2mL) was heated at 14O0C for Ih in a microwave reactor. The mixture was evaporated and the residue was purified by silica gel column chromatography using a 3:1 mixture of EtOAc and petroleum ether as eluant, to give the title compound (0.038g, 17%) as a solid;
  • 22
  • [ 52023-68-4 ]
  • [ 420-04-2 ]
  • N-(morpholin-4-ylpyridin-3-yl)guanidine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride; In 1,4-dioxane; at 20 - 95℃; for 24h; 6-Morpholino-3-pyridinamine (Ig, 5.58mmol, 1 eq) and cyanamide (293mg, 6.98mmol, 1.25 eq) were combined in 1,4-dioxane (15ml) at room temperature. A 4.0M HCl solution in 1,4-dioxane (2.1ml, 8.37mmol, 1.5eq) was added and the mixture heated to ~95C for 24 hours. After this time the mixture was concentrated and washed thoroughly with ether, yielding the crude HCl salt as a brown solid (1.52g, 94%). NMR: 3.53 (t, 4H), 3.70 (t, 4H), 7.03 (d, IH)5 7.48 (bs, 3H), 7.56 (dd, IH), 8.00 (d, IH) and 9.70 (s, IH).
  • 23
  • [ 464213-93-2 ]
  • [ 52023-68-4 ]
  • [ 37091-73-9 ]
  • N-(6-morpholinopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; Example 224 N-(6-Morpholinopyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide 3-Amino-6-morpholinopyridine (0.269 g, 1.500 mmol), triethylamine (0.197 g, 1.950 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.165 g, 0.975 mmol) were added to a methylene chloride solution (100 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.281 g, 0.750 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform: methanol = 10:1) to obtain the titled compound (0.239 g, 0.446 mmol, 59percent).
  • 24
  • [ 52023-68-4 ]
  • [ 42518-42-3 ]
  • 2-chloro-5,6-dimethyl-N-(6-morpholinopyridin-3-yl)-thieno[2,3-d]pyrimidine-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With calcium carbonate; In ethanol;Heating / reflux; To 240 mg (1.02 mmol) of 2 , 4-dichloro-5, 6-dimethyl- thieno [2, 3-d] -pyrimidine in 50 ml of ethyl alcohol were added 226.40 mg (1.26 mmol) of 6-morpholinopyridin-3- amine and 130.90 mg (1.23 mmol) of calcium carbonate, and then the mixture was stirred under reflux. After completion of the reaction, the reaction solvent, ethyl alcohol, was evaporated under reduced pressure, and the residue was crystallized from ethyl alcohol and filtered, yielding 440 mg (quantitative) of 2-chloro-5, 6-dimethyl- N- (6-morpholinopyridin-3-yl) -thenio [2, 3-d] pyrimidine -A- amine. 200 mg (0.50 mmol) of the obtained product was EPO <DP n="15"/>dissolved in 20 ml of 1-butanol in a sealed tube, and 220 mui (1.50 ramol) of triethylamine and 45.9 mg of piperazine were added thereto, and the mixture was stirred at 120 C . After completion of the reaction, the resulting solid was filtered and the filtrate was concentrated under reduced pressure and then crystallized from ethyl acetate, yielding 25 mg (12% yield) of 5,6- dimethyl-N- (beta-morpholinopyridin-3-yl) -2- (piperazin-1-yl) - thieno [2, 3-d] pyrimidine-4-amine. To 9 mg (0.02 mmol) of the obtained compound, 5, beta-dimethyl-2-piperazin-l-yl- thieno[2,3-d] pyrimidin-4-yl-4-morpholin-4-yl-phenylamine in 5 ml of dimethyl chloride were added 3.5 (jJL (0.02 mmol) of triethylamine and 4.1 mg (0.02 mmol) of picolinoyl chloride hydrochloride, and then the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solvent, dimethyl chloride, was evaporated under reduced pressure and crystallized from ethyl acetate, thus obtaining 7 mg (35% yield) of the title product. 1H NMR (CDCl3) ppm : 9.05(s, IH), 8.85-8.95(d, IH), 8.27-8.35(m, IH), 7.79-8.01(m, IH), 7.60-7.79(m, IH), 7.25-7.30(m, IH), 6.87-beta.95(m, IH), 3.72-3.50(m, 8H), 3.22-3.45(m, 8H), 2.40(s, 3H), 2.27(s, 3H), 1.59-1.51 (m, 6H)
100% With calcium carbonate; In ethanol;Heating / reflux; EXAMPLE 4Preparation of 4-[5,6-dimethyl-4-(6-morpholinopyridin-3-ylamino)-thieno[2,3-d]pyrimidin-2-yl]-piperazin-1-yl-pyridin-2-yl-methanoneTo 240 mg (1.02 mmol) of 2,4-dichloro-5,6-dimethyl-thieno[2,3-d]-pyrimidine in 50 ml of ethyl alcohol were added 226.40 mg (1.26 mmol) of 6-morpholinopyridin-3-amine and 130.90 mg (1.23 mmol) of calcium carbonate, and then the mixture was stirred under reflux. After completion of the reaction, the reaction solvent, ethyl alcohol, was evaporated under reduced pressure, and the residue was crystallized from ethyl alcohol and filtered, yielding 440 mg (quantitative) of 2-chloro-5,6-dimethyl-N-(6-morpholinopyridin-3-yl)-thenio[2,3-d]pyrimidine-4-amine. 200 mg (0.50 mmol) of the obtained product was dissolved in 20 ml of 1-butanol in a sealed tube, and 220 mul (1.50 mmol) of triethylamine and 45.9 mg of piperazine were added thereto, and the mixture was stirred at 120 C. After completion of the reaction, the resulting solid was filtered and the filtrate was concentrated under reduced pressure and then crystallized from ethyl acetate, yielding 25 mg (12% yield) of 5,6-dimethyl-N-(6-morpholinopyridin-3-yl)-2-(piperazin-1-yl)thieno[2,3-d]pyrimidine-4-amine. To 9 mg (0.02 mmol) of the obtained compound, 5,6-dimethyl-2-piperazin-1-yl-thieno[2,3-d]pyrimidin-4-yl-4-morpholin-4-yl-phenylamine in 5 ml of dimethyl chloride were added 3.5 mul (0.02 mmol) of triethylamine and 4.1 mg (0.02 mmol) of picolinoyl chloride hydrochloride, and then the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solvent, dimethyl chloride, was evaporated under reduced pressure and crystallized from ethyl acetate, thus obtaining 7 mg (35% yield) of the title product.
  • 25
  • 2-phenyl-5-(trifluoromethyl)oxazole-4-carboxylic acid [ No CAS ]
  • [ 52023-68-4 ]
  • 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; Example 1 Preparation of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide A mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (1.58 g, 6.14 mmol), <strong>[52023-68-4]6-morpholin-4-yl-pyridin-3-ylamine</strong> (1.0 g, 5.58 mmol), N-hydroxybenzotriazole (1.27 g, 8.37 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.6 g, 8.37 mmol) in anhydrous dichloromethane (20 mL) was stirred at room temperature overnight. After the reaction was complete, solvent was evaporated. The resulted mixture was mixed with water and extracted twice with ethyl acetate. The organic layers were collected, combined, washed with brine, dried over sodium sulfate, and then concentrated to give a solid. The crude product was purified by flash chromatography (Merck silica gel 60, 230-400 mesh, 0%-100% ethyl acetate in hexane) to gave 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide (1.15 g, 50%) as an off-white solid. LCMS calcd for C20H17F3N4O3 (m/e) 418, obsd 419 (M+H).
  • 26
  • [ 939376-97-3 ]
  • [ 52023-68-4 ]
  • 2-(2-chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In acetonitrile; at 85℃; Example 95 Preparation of 2-(2-chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide A mixture of 2-(2-chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (174 mg, 0.5 mmol) and <strong>[52023-68-4]6-morpholin-4-yl-pyridin-3-ylamine</strong> (90 mg, 0.5 mmol) in 5 mL of acetonitrile was stirred at 85 C. overnight. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (Merck silica gel 60, 230-400 mesh, 0-15% methanol in methylene chloride for 30 min) to yield 2-(2-chloro-phenyl)-4-ethyl-oxazole-5-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide (107 mg, 52% yield) as a light yellow solid. LCMS calcd for C21H21ClN4O3 (m/e) 412, obsd 413 (M+H).
  • 27
  • [ 939377-18-1 ]
  • [ 52023-68-4 ]
  • 5-cyclohexyl-2-methyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h; Example 118 Preparation of 5-cyclohexyl-2-methyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide 5-Cyclohexyl-2-methyl-furan-3-carboxylic acid (83 mg, 0.365 mmol), <strong>[52023-68-4]6-morpholin-4-yl-pyridin-3-ylamine</strong> (83 mg, 0.4 mmol), and triethylamine (154 uL, 1.09 mmol) were dissolved in 5 mL of DMF and chilled in an ice bath. To this solution was added BOP (169 mg, 0.383 mmol) in one portion. The mixture was stirred at room temperature for one hour and then diluted with 30 mL ethyl acetate. The ethyl acetate solution was washed with saturated sodium bicarbonate (2*10 mL) and saturated sodium chloride (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to dryness under vacuum. The crude product was purified by flash chromatography using ethyl acetate/hexane to yield 5-cyclohexyl-2-methyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide as a light grey powder (87 mg, 64%). ES-MS calcd for C21H27N3O3 (m/e) 369.5, obsd 370.3 (M+H).
  • 28
  • [ 939377-21-6 ]
  • [ 52023-68-4 ]
  • 5-cyclohexyl-2-ethyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 1h; Example 119 Preparation of 5-cyclohexyl-2-ethyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide 5-Cyclohexyl-2-ethyl-furan-3-carboxylic acid (26 mg, 0.116 mmol), <strong>[52023-68-4]6-morpholin-4-yl-pyridin-3-ylamine</strong> (20 mg, 0.116 mmol), and triethylamine (49 uL, 0.348 mmol) were dissolved in 4 mL of DMF and chilled in an ice bath. To this solution was added BOP (53 mg, 0.121 mmol) in one portion. The mixture was stirred at room temperature, for one hour and then diluted with 30 mL ethyl acetate. The ethyl acetate solution was washed with saturated sodium bicarbonate (2*10 mL) and saturated sodium chloride (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to dryness under vacuum. The crude product was purified by flash chromatography using ethyl acetate/hexane to yield 5-cyclohexyl-2-ethyl-furan-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide as a light grey powder (11.5 mg, 26%). ES-MS calcd for C22H29N3O3 (m/e) 383.5, obsd 384 (M+H).
  • 29
  • [ 638218-95-8 ]
  • [ 52023-68-4 ]
  • [ 144-55-8 ]
  • 2-methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzofuran-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77 mg (74%) With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; N,N-dimethyl-formamide; Example 102 2-Methyl-6-(thieno[3,2-b]pyridin-7-yloxy)benzofuran-3-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)amide A solution of 2-methyl-6-[thieno[3,2-b]pyridin-7-yloxy]benzofuran-3-carboxylic acid 100 (70 mg, 0.215 mmole), 6-Morpholin-4-yl-pyridin-3-ylamine (77 mg, 0.43 mmole), HATU (163 mg, 0.43 mmole), and diisopropylethylamine (75 mul, 0.43 mmole) were stirred in DMF 2 ml) at ambient temperature for 17 hr. The mixture was then added dropwise to a solution of cold aqueous NaHCO3 resulting in a precipitate which was collected by filtration. This material was purified on silica gel using a gradient of 0 to 5% methanol in a 1:1 mixture of ethyl acetate and dichloromethane as eluent to give 77 mg (74%) of a lavander solid. 1H NMR (CD3CN) delta8.50 (1H, d, J=5.3 Hz), 8.37 (1H, d, J=2.5 Hz), 8.29 (1H, s), 7.92-7.88 (3H, m), 7.54 (1H, d, J=5.3 Hz), 7.45 (1H, d, J=2.0 Hz), 7.23 (1H, dd, J=8.6, 2.0 Hz), 6.78 (1H, d, J=9.1 Hz), 6.64 (1H, d, J=5.3 Hz), 3.76 (4H, t, J=4.9 Hz), 3.44 (4H, t, J=4.9 Hz), 2.72 (3H, s). Anal. Calcd for C26H22N4O4S: C, 64.18; H, 4.56; N, 11.52; S, 6.59. Found: C, 64.42; H, 4.77; N, 11.32; S, 6.50.
  • 30
  • [ 52023-68-4 ]
  • [ 530-62-1 ]
  • [ 1118915-93-7 ]
YieldReaction ConditionsOperation in experiment
70% 6-morpholinopyridin-3 -amine (3.59g, 20mmol) in 50 ml CH2Cl2WaS added to the solution N,N'-carbonyldiimidazole (CDI) (4.Og , 25 mmol) in 100ml CH2Cl2, and the solution was mix at RT for 1 h. Solvent were removed on rotary evaporator and the residue was dissolved in 50ml dioxane and treated with hydrazine (6.5 ml , 200mmol, 10eq) at RT to 450C for Ih. The reaction mixture was subjected to EtO Ac/aqueous workup to remove excess hydrazine The aqueous solution was extracted with CH2Cl2 The organic layer was dried over Na2SO4,filtered evaporated in vacuo gave N-(6- morpholinopyridin-3-yl)hydrazinecarboxamide (1) (3.32g, 70%) as a light brown solid.
  • 31
  • [ 52023-68-4 ]
  • [ 1126430-46-3 ]
  • [ 1126430-88-3 ]
YieldReaction ConditionsOperation in experiment
7% With hydrogenchloride; In 1,4-dioxane; isopropyl alcohol; at 180℃; for 0.333333h;Microwave irradiation; To a suspension containing 0.1 g (0.28 mmol) of 5-(2-chloro-4-pyrimidinyl)-lambda/-ethyl-4- [3-methyl-5-(methyloxy)phenyl]-1 ,3-thiazol-2-amine, prepared by a procedure analogous to Example 25, Step F, 0.06 g (0.33 mmol) of 6-(4-morpholinyl)-3- pyridinamine and 1 ml. of iPrOH was added 0.1 ml. of a 4.0 M solution of HCI in dioxane. The reaction mixture was heated at 1800C in a microwave reactor for 20 min and the solvent was removed under reduced pressure. The residue was subjected to silica gel chromatography and further purified by HPLC to give 10 mg (7%) of 4-{2-(ethylamino)-4-[3-methyl-5-(methyloxy)phenyl]-1 ,3-thiazol-5-yl}-lambda/-[6-(4- morpholinyl)-3-pyridinyl]-2-pyrimidinamine as a yellow solid: 1H NMR (400 MHz,DMSOd6) delta 9.26 (s, 1 H), 8.49 (d, J = 2.6 Hz, 1 H), 8.21 (t, J = 5.4 Hz, 1 H), 8.03 (d, J = 5.1 Hz, 1 H), 7.89 (dd, J = 9.3, 2.7 Hz, 1 H), 6.88 (s, 1 H), 6.84 (s, 1 H), 6.79 - 6.82 (m, 2 H), 6.24 (d, J = 5.3 Hz, 1 H), 3.73 (s, 3 H), 3.70 - 3.73 (m, 4 H), 3.33 - 3.37 (m, 6 H), 3.30 (dd, J = 5.2 and 1.7 Hz, 2 H), 2.55 (dt, J = 3.8 and, 1.8 Hz, 2 H), 2.31 (s, 3 H), and 1.18 (t, J = 7.1 Hz, 3 H). HRMS Calcd for C26H30N7O2S (M+H+): 504.2182. Found: 504.2192.
  • 32
  • [ 52023-68-4 ]
  • [ 1126431-74-0 ]
  • [ 1126431-73-9 ]
YieldReaction ConditionsOperation in experiment
45% With toluene-4-sulfonic acid; In 2,2,2-trifluoroethanol; water; at 160℃; for 1h;Microwave irradiation; A solution of 2-chloro-4-{2-(1-methylethyl)-4-[3-methyl-5-(methyloxy)phenyl]-1 ,3- thiazol-5-yl}pyrimidine (250 mg, 0.695 mmol), 6-(4-morpholinyl)-3-pyridinamine (149 mg, 0.834 mmol), prepared by a procedure analogous to Example 35, Step B, and p-toluenesulfonic acid hydrate (264 mg, 1.39 mmol) in trifluoroethanol (2.8 ml.) was heated in a microwave at 1600C for 1 h. The reaction mixture was concentrated onto silica gel. Purification by flash column chromatography (0 to 100% (15% MeOH/1% NH4OH/DCM):EtOAc) afforded 157 mg (45%) of the title compound of Example 61. 1H NMR (400 MHz, DMSO-d6): delta 9.49 (s, 1 H), 8.44 (d, 1 H, J = 2.8 Hz), 8.26 (d, 1 H, J = 5.3 Hz), 7.88 (dd, 1 H, J = 2.8, 9.0 Hz), 6.94 (s, 1 H), 6.85 (s, 2H), 6.81 (d, 1 H, J = 9.2 Hz), 6.47 (d, 1 H, J = 5.3 Hz), 3.71 (m, 7H), 3.36 (m, 4H), 3.29 (m, 1 H), 2.31 (s, 3H), and 1.38 (d, 6H, J = 6.8 Hz); MS (ESI): 503.21 [M+H]+.
  • 33
  • [ 52023-68-4 ]
  • [ 1160625-42-2 ]
  • [ 76-05-1 ]
  • N-(3-(2-ethyl-5-(2-((6-(4-morpholinyl)-3-pyridinyl)amino)-4-pyrimidinyl)-1,3-thiazol-4-yl)phenyl)-2,6-difluorobenzamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% Step C: lambda/-{3-[2-Ethyl-5-(2-[6-(4-morphoIinyI)-3-pyridinyl]amino}-4-pyrimidinyl)-1 ,3- thiazol-4-yl]phenyl}-2,6-difluorobenzamide trifluoroacetate; A/-{3-[5-(2-Chloro-4-pyrimidinyl)-2-ethyl-1 ,3-thiazol-4-yI]phenyl}-2,6- difluorobenzamide (100 mg, 0.22 mmol), prepared by a procedure analogous to Example 112, Step A, was combined with 6-(4-morpholinyl)-3-pyridinamine (36 mg, 0.20 mmol), para-toluenesulfonic acid monohydrate (45 mg, 0.24 mmol) and 2,2,2- trifluoroethanol (3 ml_) in a sealed vessel. The reaction was heated for 60 min at 1700C by microwave radiation. The reaction was cooled and treated with NaHCO3 (200 mg). The reaction was stirred for 15 min before being concentrated to a residue and purified by silica gel chromatography (gradient: 5-100%(80%CH2CI2: 190ZOMeOHIi0ZoNH4OH)ZCH2CI2). The fractions with coupled adduct were combined and concentrated under vacuum to a brown oil. The residue was purified a second time by RP HPLC (C18; 10-100% acetonitrile (0.1% TFA)/H2O (0.1% TFA)). The second purification yielded 6 mg (4%) of the title compound of Example 118 as the trifluoroacetate salt. 1H-NMR (400 MHz, MEOH-d4) delta 8.69 (d, J = 2.6 Hz, 1 H), 8.30 (d, J = 5.3 Hz, 1 H), 8.10 (dd, J = 9.8, and 2.5 Hz, 1 H), 7.91 (s, 1 H), 7.65 - 7.71 (m, 1 H), 7.43 - 7.54 (m, 2 H), 7.35 (s, 1 H), 7.30 - 7.34 (m, 1 H), 7.07 (t, J = 8.1 Hz, 2 H), 6.71 (d, J = 5.3 Hz, 1 H), 3.82 - 3.89 (m, 4 H), 3.56 - 3.63 (m, 4H), 3.08 (q, J = 7.6 Hz, 2 H), and 1.44 (t, J = 7.5 Hz, 3 H); m/z (ESI): 600.15 [M+H]+.
  • 34
  • [ 896160-38-6 ]
  • [ 52023-68-4 ]
  • 5-[3-(1-cyano-1-methylethyl)benzoyl]amino}-2-methyl-N-(6-morpholin-4-ylpyridin-3-yl)benzamide [ No CAS ]
  • 35
  • [ 52023-68-4 ]
  • [ 1190379-94-2 ]
  • [ 1190378-60-9 ]
YieldReaction ConditionsOperation in experiment
18% With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere; Intermediate 8 (40 mg, 0.130 mmol), 6-mophiholin-4-yl-pyridin-3-ylamine (28 mg, 0.155 mmol), Pd2(dba)3 (7 mg, 0.008 mmol), xantphos (6 mg, 0.01 mmol) and sodium te/Y-butoxide (37 mg, 0.385 mmol) were combined with dioxane (1 ml), sealed and then purged with nitrogen gas. The reaction mixture was heated at 90 0C for 18 hours, evaporated and purified through a silica plug, eluting with 0 to 10% methanol/DCM. The crude product was triturated with diethyl ether, filtered and dried to give the desired product as a white solid (10 mg, 18%). 1H NMR (400 MHz, DMSO- d6) delta ppm 0.40 - 0.48 (m, 2 H), 0.76 - 0.85 (m, 2 H), 1.39 - 1.50 (m, 1 H), 1.62 - 1.78 (m, 3 H), 1.79 - 1.92 (m, 1 H), 1.92 - 2.02 (m, 2 H), 2.04 - 2.16 (m, 2 H), 2.90 - 3.01 (m, 1 H), 3.08 - 3.15 (m, 2 H), 3.28 - 3.33 (m, 4 H), 3.35 - 3.42 (m, 2 H), 3.67 - 3.73 (m, 4 H), 6.73 - 6.82 (m, 2 H), 7.56 (s, 1 H), 7.63 - 7.71 (m, 1 H), 7.97 (dd, /=9.2, 2.7 Hz, 1 H), 8.42 - 8.46 (m, 1 H), 8.67 (br. s, 1 H); m/z (ES+APCI)+: 452 [M+H]+.
 

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Technical Information

Categories

Related Functional Groups of
[ 52023-68-4 ]

Amines

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[ 52023-68-4 ]

Morpholines

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2-Bromo-6-morpholinopyridine

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