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[ CAS No. 39643-31-7 ] {[proInfo.proName]}

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Chemical Structure| 39643-31-7
Chemical Structure| 39643-31-7
Structure of 39643-31-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 39643-31-7 ]

CAS No. :39643-31-7 MDL No. :MFCD00047467
Formula : C11H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :OYECAJPUPWFCSL-UHFFFAOYSA-N
M.W : 176.26 Pubchem ID :458795
Synonyms :

Safety of [ 39643-31-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 39643-31-7 ]

* 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 [ 39643-31-7 ]

[ 39643-31-7 ] Synthesis Path-Downstream   1~11

  • 2
  • [ 13529-17-4 ]
  • [ 39643-31-7 ]
  • 5-formyl-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 5-Formyl-2-furancarboxylic acid; 2-piperidin-1-yl-phenylamine With benzotriazol-1-ol; triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane 4.A EXAMPLE 4-A; 5-(2-PIPERIDIN-L-YL-PHENYLCARBAMOYL)-FURAN-2-CARBOXYLIC acid A solution OF 5-FORMYL-2-FURANCARBOXYLIC acid (TCI) (1.0 mmol), 2- piperidinoaniline (1.0 mmol), HOBT (1.2 mmol), and Et3N (2 mmol) in DCM (10 mL) was stirred for 10 min at room temperature. EDCI (1.2 mmol) was then added and the resulting orange solution was stirred overnight. The reaction mixture was treated with saturated NAHC03 solution (10 mL) and extracted with DCM. The combined organic layers were dried over MGS04, and concentrated under reduced pressure to afford the crude product as an orange solid. Purification by silica gel chromatography afforded the amidoaldehyde product in 80 % yield. The aldehyde product (1 mmol) was dissolved IN H20/DIMETHOXYETHANE ("DME") (2: 1,5 mL) containing sodium carbonate ("NA2C03") (2 mol). In a separate flask, potassium permanganate ("KMNO4") (1.3 mmol) was dissolved in HA0 (5 mL) and was slowly added to the reaction flask at 45 °C. The reaction was stirred overnight at room temperature, filtered through a plug of celite, and then acidified to a pH of 3 to 4 using a hydrochloric acid ("HC1") solution (1 N). The product, which precipitated out as a white solid, was filtered, washed with H2O and dried under high vacuum to afford pure product. MS: 315 (M+1). 1H NMR (DMSO-D6, 300 MHZ) : 8 13. 60 (br s, 1H), 9.90 (s, 1H), 8.25 (dd, 1H), 7.36 (dd, 2H), 7.35-7. 25 (m, 1H), 7.20-7. 10 (m, 2H), 2.85-2. 65 (m, 4H), 1.85-1. 65 (m, 4H), 1.65-1. 45 (m, 2H).
80% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 4-A EXAMPLE 4-A; 5-(2-Piperidin-l-yl-phenylcarbamoyl)-furan-2-carboxvlic acid; A solution of 5-formyl-2-furancarboxylic acid (TCI) (1.0 mmol), 2-piperidinoaniline (1.0 mmol), HOBT (1.2 mmol), and Et3N (2 mmol) in DCM (10 mL) was stirred for 10 min at room i temperature. EDCI (1.2 mmol) was then added and the resulting orange solution was stirred Overnight. The reaction mixture was treated with saturated NaHCO3 solution (10 mL) and extracted with DCM. The combined organic layers were dried over MgSO4, and concentrated under reduced pressure to afford the crude product as an orange solid. Purification by silica gel chromatography afforded the amidoaldehyde product in 80 % yield. The aldehyde product (1 mmol) was dissolved in H2θ/dimethoxyethane ("DME") (2:1, 5 mL) containing sodium carbonate ("Na2CO3") (2 mol). In a separate flask, potassium permanganate ("KMnO4") (1.3 mmol) was dissolved in H2O (5 mL) and was slowly added to the reaction flask at 45 0C. The reaction was stirred overnight at room temperature, filtered through a plug of celite, and then acidified to a pH of 3 to 4 using a hydrochloric acid ("HCl") solution (1 N). The product, which precipitated out as a white solid, was filtered, washed with H2O and dried under high vacuum to afford pure product. MS: 315 (M+l). 1H NMR (DMSO^65 SOO MHZ): δ 13.60 (br s, IH), 9.90 (s, IH), 8.25 (dd, IH), 7.36 (dd, 2H), 7.35-7.25 (m, IH), 7.20-7.10 (m, 2H), 2.85-2.65 (m, 4H), 1.85-1.65 (m, 4H), 1.65-1.45 (m, 2H).
  • 3
  • [ 400743-82-0 ]
  • [ 20012-63-9 ]
  • [ 39643-31-7 ]
  • [ 728918-72-7 ]
  • C8H7F4N [ No CAS ]
  • C33H29IN5O4Pol [ No CAS ]
  • [ 91646-45-6 ]
  • [ 4273-98-7 ]
  • [ 2264-92-8 ]
  • [ 1204-44-0 ]
  • [ 68817-71-0 ]
  • [ 369-36-8 ]
  • [ 37750-29-1 ]
  • [ 55751-54-7 ]
  • [ 18595-14-7 ]
  • [ 52562-19-3 ]
  • [ 62532-99-4 ]
  • [ 21627-58-7 ]
  • [ 73818-73-2 ]
  • [ 54705-91-8 ]
  • [ 26286-54-4 ]
  • [ 177171-13-0 ]
  • [ 99-55-8 ]
  • [ 23491-48-7 ]
  • [ 400750-84-7 ]
  • C42H37N8O4Pol [ No CAS ]
  • C42H37N8O4Pol [ No CAS ]
  • C43H43N6O4Pol [ No CAS ]
  • C42H39N6O4Pol [ No CAS ]
  • C43H37N6O4PolS [ No CAS ]
  • C40H36N7O6Pol [ No CAS ]
  • C42H39N6O6Pol [ No CAS ]
  • C39H33FN7O6Pol [ No CAS ]
  • C44H39N6O5Pol [ No CAS ]
  • C45H38ClN6O4Pol [ No CAS ]
  • C46H41N6O4Pol [ No CAS ]
  • C43H42N7O4Pol [ No CAS ]
  • C46H41N6O5Pol [ No CAS ]
  • C45H38FN6O4Pol [ No CAS ]
  • C45H38ClN6O4Pol [ No CAS ]
  • C41H35F4N6O4Pol [ No CAS ]
  • C45H39N6O6PolS [ No CAS ]
  • C45H38ClN6O4PolS [ No CAS ]
  • C44H44N7O4Pol [ No CAS ]
  • C47H41N6O5Pol [ No CAS ]
  • C45H39ClN7O4Pol [ No CAS ]
  • C47H41N6O6Pol [ No CAS ]
  • C45H45N8O5Pol [ No CAS ]
  • C44H44N9O6Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ISOPROPYLAMIDE; at 60℃;Combinatorial reaction / High throughput screening (HTS); Step 2. Catalytic amination of the solid supported 8-iodo-l-methyl-4,5-dihydro- lH-pyrazolo [4,3-h] quinazoline-3-carboxamide; <n="82"/>Using a 4 niL Argonaut Trident synthesizer cassette, 200 mg (0.11 mmol) of the resin from step 1 above, were charged into separate vials. To each of the reactor vials flushed with argon, finely divided potassium carbonate (0.15 g, 1.1 mmol), palladium acetate [Pd(OAc)2] (2.5mg, 0.011 mmol, 10%), (HK)-BINAP (6.8 mg, 0.011 mmol, 10%) and the corresponding amine (0.22 mmol, 2 equivalents) in degassed (argon) dimethyacetamide (2 mL) were added. The resulting mixture was agitated at 600C for 10 hours on the Argonaut Trident Automated Library Synthesizer (ALS) station. The Trident ALS station was programmed to continuously mechanically agitate the resin at 6O0C while a nitrogen gas "sparge" was incorporated to re-suspend the scarcely soluble potassium carbonate. Nitrogen gas sparging was incorporated once per hour, for a 30 second duration, throughout the 16-hour heating cycle.The resin was drained from the synthesis cocktail and washed using the Argonaut Trident External Agitation Thermal Unit (EATU) synthesis station with DMA (3 x 2 mL, 5 min.). The above catalytic amination cycle was repeated a second time using the previously described procedure.Upon completion of the second amination cycle, the resin was drained from the synthesis cocktail and washed using the Argonaut Trident EATU synthesis station with DMF (1 x 2 mL, 5 min.), with water (1 x 2 mL, 5 min.), with DMF/water (1 : 1) (3 x 2 mL, 5 min.), with DMF (3 x 2 mL, 5 min.), with methanol (3 x 2 mL, 5 min.) and with DCM (3 x 2 mL, 5 min.).
  • 5
  • [ 3973-08-8 ]
  • [ 39643-31-7 ]
  • [ 1458537-35-3 ]
  • 6
  • [ 16042-25-4 ]
  • [ 39643-31-7 ]
  • [ 1469925-02-7 ]
  • 7
  • [ 49609-84-9 ]
  • [ 39643-31-7 ]
  • 2-chloro-N-(2-(piperidin-1-yl)phenyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 2-piperidin-1-yl-phenylamine With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 2-Chloronicotinoyl chloride In dichloromethane for 0.5h; 3.2.3. Synthesis of Compounds III: 2-Chloro-N-(2-(piperidin-1-yl)phenyl)nicotinamide (1b) A solution of 2-(piperidin-1-yl)aniline (0.2 g, 0.025 mol), dichloromethane (25 mL) and triethylamine (0.5 mL) was added to a 50 mL flask and cooled to 0 °C in an ice bath. After ten minutes, 2-chloronicotinoyl chloride (0.22 g) was added [20,21]. The mixture was stirred for 30 min, and then concentrated under reduced pressure to give a crude product. The pure 2-chloro-N-(2-(piperidin-1-yl)phenyl) nicotinamide (1b) was obtained by column chromatography (EtOAc:PE = 8:1) purification.yield 88%; yellow powder; mp 76-77 °C; 1H-NMR (CDCl3) δ 9.77 (s, 1H, NH), 8.53 (dd, J = 4.8,2.0 Hz, 2H, pyridyl-H), 8.22 (dd, J = 7.7, 2.0 Hz, 1H, pyridyl-H), 7.42 (dd, J = 7.7, 4.8 Hz, 1H, Ar-H), 7.25-7.06 (m, 3H, Ar-H), 2.93 (s, 2H, CH2), 2.71 (s, 2H, CH2), 1.88-1.64 (m, 2H, CH2), 1.44-1.22 (m,2H, CH2), 0.97 (d, J = 6.4 Hz, 2H, CH2); 13C-NMR (CDCl3) δ 162.10, 150.81, 146.72, 142.92, 139.71,133.20, 131.83, 125.24, 124.31, 122.62, 120.93, 119.21, 53.90, 26.44, 23.62; HRMS (ESI), m/z calcdfor C17H19ClN3O (M+H)+ 316.1212, found 316.1211.
  • 8
  • [ 58757-38-3 ]
  • [ 39643-31-7 ]
  • 6-chloro-N-(2-(piperidin-1-yl)phenyl)nicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-piperidin-1-yl-phenylamine With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: 6-Chloronicotinoyl chloride In dichloromethane for 0.5h; 3.2.3. Synthesis of Compounds III: 2-Chloro-N-(2-(piperidin-1-yl)phenyl)nicotinamide (1b) General procedure: A solution of 2-(piperidin-1-yl)aniline (0.2 g, 0.025 mol), dichloromethane (25 mL) and triethylamine (0.5 mL) was added to a 50 mL flask and cooled to 0 °C in an ice bath. After ten minutes, 2-chloronicotinoyl chloride (0.22 g) was added [20,21]. The mixture was stirred for 30 min, and then concentrated under reduced pressure to give a crude product. The pure 2-chloro-N-(2-(piperidin-1-yl)phenyl) nicotinamide (1b) was obtained by column chromatography (EtOAc:PE = 8:1) purification yield 88%;
  • 9
  • [ 5555-00-0 ]
  • [ 39643-31-7 ]
  • 2-methyl-N-(2-(piperidin-1-yl)phenyl)furan-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: A solution of 2-(piperidin-1-yl)aniline (0.2 g, 0.025 mol), dichloromethane (25 mL) and triethylamine (0.5 mL) was added to a 50 mL flask and cooled to 0 C in an ice bath. After ten minutes, 2-chloronicotinoyl chloride (0.22 g) was added [20,21]. The mixture was stirred for 30 min, and then concentrated under reduced pressure to give a crude product. The pure 2-chloro-N-(2-(piperidin-1-yl)phenyl) nicotinamide (1b) was obtained by column chromatography (EtOAc:PE = 8:1) purification yield 88%;
  • 10
  • [ 39643-31-7 ]
  • [ 82964-91-8 ]
  • 4-(methylsulfonyl)-N-(2-(piperidin-1-yl)phenyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
2% With pyridine at 115℃; for 1h; Microwave irradiation; 4 Example 4 (0134) 4-(methylsulfonyl)-N-(2-(piperidin-l-yl)phenyl)benzenesulfonamide A solution of 2-(piperidin-l-yl)aniline (0.176 g, 1 mmol) in pyridine (Volume: 2 ml) was treated with 4-(methylsulfonyl)benzene-l-sulfonyl chloride (0.255 g, 1.000 mmol). The solution was microwaved at 115°C for 1 hr. To the solution was added toluene (2ml). The solution was concentrated. To the residue was added MeOH (1 ml). The crude product was purified by reversed-phase chromatography (4-100% CTbCN over 15 min) to give desired product (0.002g, 2% yield). (LCMS, ESI pos.) Calculated for C18H22N2O4S2: 395.1 (M + H), Measured: 395.1. NMR (400 MHz, DMSO-d6) d 9.18 (s, 1H), 8.19 - 8.11 (m, 2H), 8.10 - 8.03 (m, 2H), 7.29 (dd, J = 7.5, 1.2 Hz, 1H), 7.20 - 7.13 (m, 2H), 7.09 (ddd, J = 7.8, 5.7, 3.2 Hz, 1H), 3.31 (s, 3H), 2.52 - 2.47 (m, 4H), 1.63 - 1.41 (m, 6H).
  • 11
  • [ 39643-31-7 ]
  • [ 954377-22-1 ]
  • N-[2-(1-piperidinyl)phenyl]-5-(trifluoromethyl)thiophene-2-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.9% With trimethylamine In dichloromethane at 0 - 20℃; 48.4 Step 4 To a stirred solution of compound 48C (320 mg, 1.3 mmol, 1 eq) and compound 4F (224 mg, 1.3 mmol, 1 eq) in di chloromethane was added tri ethylamine (262 mg, 2.6 mmol, 2 eq) at 0 °CO The reaction was allowed to warm to room temperature and stirred overnight. TLC showed the reaction was completed. The reaction was concentrated in vacuum and the residue was purified by flash chromatography on silica gel (0-15% of ethyl acetate in petroleum ether) to afford compound 48 (25 mg, HPLC=99.0%, Yield=4.9%) as a white solid. MS-ESI: [M+l]+= 391.0 'H NMR (400 MHz, CDCI3): δ 8.30 (br, 1H), 7.64 (d, 1H), 7.42 (br, 1H), 7.31 (d, 1H), 7.17-7.11 (m, 3H), 2.76-2.27 (m, 4H), 1.82-1.69 (m, 6H).
4.9% With trimethylamine In dichloromethane at 0 - 20℃; 48.4 Step 4 To a stirred solution of compound 48C (320 mg, 1.3 mmol, 1 eq) and compound 4F (224 mg, 1.3 mmol, 1 eq) in di chloromethane was added tri ethylamine (262 mg, 2.6 mmol, 2 eq) at 0 °CO The reaction was allowed to warm to room temperature and stirred overnight. TLC showed the reaction was completed. The reaction was concentrated in vacuum and the residue was purified by flash chromatography on silica gel (0-15% of ethyl acetate in petroleum ether) to afford compound 48 (25 mg, HPLC=99.0%, Yield=4.9%) as a white solid. MS-ESI: [M+l]+= 391.0 'H NMR (400 MHz, CDCI3): δ 8.30 (br, 1H), 7.64 (d, 1H), 7.42 (br, 1H), 7.31 (d, 1H), 7.17-7.11 (m, 3H), 2.76-2.27 (m, 4H), 1.82-1.69 (m, 6H).
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