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[ CAS No. 5308-28-1 ]

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Chemical Structure| 5308-28-1
Chemical Structure| 5308-28-1
Structure of 5308-28-1 * Storage: {[proInfo.prStorage]}

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Product Details of [ 5308-28-1 ]

CAS No. :5308-28-1 MDL No. :MFCD00190596
Formula : C8H18N2 Boiling Point : 184.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :142.24 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5308-28-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5308-28-1 ]

  • Downstream synthetic route of [ 5308-28-1 ]

[ 5308-28-1 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 5308-28-1 ]
  • [ 22117-85-7 ]
  • [ 102535-28-4 ]
  • 2
  • [ 5308-28-1 ]
  • [ 102359-00-2 ]
  • [ 102358-81-6 ]
  • 3
  • [ 5308-28-1 ]
  • [ 93107-30-3 ]
  • 1-Cyclopropyl-6-fluoro-7-(4-isobutyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid [ No CAS ]
  • 4
  • [ 629625-93-0 ]
  • [ 5308-28-1 ]
YieldReaction ConditionsOperation in experiment
86.2% With palladium 10% on activated carbon; hydrogen at 20℃; for 20h; 1-Cyclohexylpyrrolidin-3-amine I-6 General procedure: To a solution of compound I-5 (240 mg) in HFIP (8 mL), 10% Pd/C (120 mg) was added and thenthe reaction mixture was stirred under H2 at room temperature and 1atm for 20 h. Then themixture was filtrated and the filtrate was concentrated to give compound I-6 as yellow oil (100 mg,75%).
With hydrogen In ethanol at 20℃; for 12h; 2 Benzyl 1-piperazinecarboxylate (1.1 g, 5.00 mmol) and isobutylaldehyde (0.91 mL, 10.0 mmol) were dissolved in 30 mL of tetrahydrofuran, and acetic acid (0.57 mL, 10.0 mmol) and sodium triacetoxyborohydride (2.11 g, 10.0 mmol) were added thereto, and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was mixed with a 1N aqueous solution of sodium hydroxide, extracted with ethyl acetate twice, and the combined organic layers were washed with brine once. The mixture was dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Fuji Silysia, NH Silica gel; ethyl acetate:hexane=50:50) to give benzyl 4-isobutylpiperazin-1-carboxylate (1.05 g) as a colorless oil. The resulting benzyl 4-isobutylpiperazin-1-carboxylate (1.05 g) was dissolved in 35 mL of ethanol, 10% palladium-carbon (750 mg) was added thereto, and the reaction mixture was stirred at room temperature under hydrogen atmosphere (1 atm) for 12 hours. The palladium-carbon was removed by filtration, and the filtrate was evaporated to give the title compound (610 mg) as a colorless oil.1H-NMR Spectrum (CDCl3,400MHz) δ(ppm): 0.90(6H,d,J=6.8Hz), 1.71-1.86(1H,m),2.07(2H,d,J=7.6Hz),2.33-2.43(4H,m),2.86-2.93(4H,m).
  • 5
  • 1-(isobutyl)-4-(4-nitrophenylpiperazine) [ No CAS ]
  • 1-(isobutyl)-4-(4-nitrophenyl)piperazine [ No CAS ]
  • [ 5308-28-1 ]
  • 4-[4-(isobutyl)-1-piperazinyl]benzenamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In ethanol 14.E.B B. B. 4-[4-(isobutyl)-1-piperazinyl]benzenamine A mixture of 1-(isobutyl)-4-(4-nitrophenylpiperazine) (9.4 g, 35.7 mmol) (from Step A above) and 10% palladium-on-charcoal in ethanol (175 mL) was hydrogenated at room temperature at 20 psi for 1.25 hour. The catalyst was filtered off and the filter cake washed thoroughly with ethanol. The mixture was evaporated under reduced pressure to give 4-[4-(isobutyl)-1-piperazinyl] benzenamine (7.8 g, 94%) as a dark red solid.
  • 6
  • [ 5308-28-1 ]
  • [ 84468-15-5 ]
  • 1-(5-isoquinolinesulfonyl)-4-isobutylpiperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With sodium hydroxide; potassium carbonate In chloroform methanol; chloroform 9 EXAMPLE 9 EXAMPLE 9 In 30 ml of chloroform were added 1.42 g of 1-isobutylpiperazine and 2.76 g of potassium carbonate, and to the mixture was added dropwise 50 ml of a chloroform solution containing 2.28 g of 5-isoquinolinesulfonyl chloride under cooling with ice. After the dropwise addition of the chloroform solution, the mixed solution thus obtained was stirred at a temperature of 15° C. to 25° C. for two hours, and then the reaction solution was washed with 20 ml of a 1N aqueous sodium hydroxide solution and extracted twice with a 5N aqueous hydrochloric acid solution. The aqueous hydrochloric acid layer was rendered alkaline, extracted three time with 30 ml of chloroform, and the chloroform layer extracted was washed with water and dried with anhydrous magnesium sulfate. After the chloroform was distilled therefrom under reduced pressure, the residue obtained was subjected to a silica gel column chromatography (silica gel: 100 g; solvent: 2% methanol-chloroform) to give 2.60 g of 1-(5-isoquinolinesulfonyl)-4-isobutylpiperazine, i.e., Compound (47) in a yield of 78%. Melting point (the dihydrochloride recrystallized from ethanol): 234° C. Mass spectrum (m/e): 333(M+), 290(M-C3 H7), 141 and 128 NMR spectrum (CDCl3, δ): 0.8(6H, d, 2*CH3), 1.2-2.0(1H, m, CH), 2.0-3.3(10H, 5*NCH2), 7.6-8.8(5H) and 9.3(1H, s) IR absorption spectrum (νmax,cap cm-1): 3430, 1620, 1350, 1340, 1170 and 1145.
  • 7
  • [ 5308-28-1 ]
  • [ 662116-67-8 ]
  • [ 942948-54-1 ]
YieldReaction ConditionsOperation in experiment
60% With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 45℃; for 18h; 36 5-Chloro-4-(4-isobutylpiperazin-1-yl)-3-nitropyridin-2-amine To a mixture of 2-amino-4,5-dichloro-3-nitropyridine (0.060 g, 0.29 mmol) and isopropanol (4.5 ml) was added 1-isobutyl-piperazine (0.045 g, 0.32 mmol) with the aid of isopropanol (0.5 ml) followed by diisopropylethylamine (0.06 ml, 0.32 mmol). The reaction mixture was heated at 45° C. for 18 h, then allowed to cool to room temperature, and concentrated in vacuo. The residue was absorbed on silica gel, the free running powder was placed on a 10 g isolute silica column which was eluted with ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as an orange solid (0.054 g, 60%); 1H-NMR (500 MHz, DMSO-d6) 0.87 (d, J=6.57 Hz, 6H, CH(CH3)2), 1.77 (m, 1H, CH(CH3)2), 2.08 (d, J=7.39 Hz, 2H, N-CH2), 2.45 (br s, 4H, piperazine N(CH2)2), 3.05 (br s, 4H, piperazine N(CH2)2), 6.94 (s, 2H, NH2), 8.06 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z): Rt=1.70 min-314, 316 [(M+H)+, Cl isotopic pattern].
  • 8
  • [ 5308-28-1 ]
  • [ 942947-95-7 ]
  • [ 942948-47-2 ]
YieldReaction ConditionsOperation in experiment
63% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 45℃; for 20h; To a mixture of <strong>[942947-95-7]5-bromo-4-chloro-3-nitro-pyridin-2-ylamine</strong> (0.126 g, 0.50 mmol) and isopropanol (9 ml) was added 1-isobutylpiperazine (0.078 g, 0.55 mmol) with the aid of isopropanol (5 ml) followed by diisopropylethylamine (0.10 ml, 0.57 mmol). The reaction mixture was heated at 45 C. for 20 h, then allowed to cool to room temperature. The precipitate was collected by filtration and washed with isopropanol and diethyl ether. The title compound was thus obtained as a yellow solid (0.112 g, 63%). 1H-NMR (500 MHz, DMSO-d6) 0.87 (d, J=6.56 Hz, 6H, CH(CH3)2), 1.77 (m, 1H, CH(CH3)2), 2.08 (d, J=7.35 Hz, 2H, N-CH2), 2.47 (br s, 4H, piperazine N(CH2)2), 3.04 (br s, 4H, piperazine N(CH2)2), 6.96 (s, 2H, NH2), 8.15 (s, 1H, 6-H);LC (Method B)-MS (ESI, m/z): Rt=1.80 min-358, 360 [(M+H)+, Br isotopic pattern].
  • 9
  • [ 5308-28-1 ]
  • [ 27514-08-5 ]
  • [ 1214265-89-0 ]
YieldReaction ConditionsOperation in experiment
54% Preparation 16: 4-(4-i-Butylpiperazin-l-yl)cyclohexanamine (cis and trans isomers); [0126] In a 250 mL flask, <strong>[27514-08-5]4-acetamidocyclohexanone</strong> (5.47 g, 35.2 mmol), N-i-butyl piperazine (10 g, 70.3 mmol) were dissolved in dry toluene (75 mL) and added methanesulfonic acid (MSA) (250 muL) and refluxed using Dean-Stark apparatus for five hours with occasional decanting toluene from Dean-Stark apparatus 3-4 times. Then removed half of the toluene from the apparatus and cooled to 500C and added 75 mL ethanol then removed the Dean-Stark apparatus and cooled to 15-200C. Added NaBH4 (35.2 mmol) portion wise under nitrogen atmosphere. Continued stirring the reaction for overnight. Then added NaBH4 (50 mmols), after 30 min added 12 rnL of 4 N HCl drop wise to the reaction. The volatiles were removed from the reaction under reduced pressure. Basified the gummy solid reaction mixture with 12 mL sat.K^CCh, diluted with another 12 mL water and further basified with 50% NaOH solution to pH about 13. Then added EtOAc (100 mL) and filtered the solid product and washed with EtOAc and ether and collected N-(4-(4-i-burtylpiperazin-l-yl)cyclohexyl)acetamide (cis and trans isomers) as white powder (5.3 g, 54%). ESI-MS: m/z 282 (M+H)+. N-(4-(4-propylpiperazin-l- yl)cyclohexyl)acetamide (5.2 g, 18.5 mmol) was refluxed in 24% cone. HCl solution for 20 hours at 115C. Then evaporated the solution under reduced pressure and the solid product obtained was dissolved and recrystallized from isopropyl alcohol to get the product as white hydrochloride salt (5.2 g). ESI-MS: m/z 240 (M+H) +.
  • 10
  • [ 5308-28-1 ]
  • [ 1245318-94-8 ]
  • [ 1245319-23-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 70℃; for 6h; 190 To a solution of 5-amino-7-chloro-2-(4-fluorophenyl)-oxazolo[5,4-d]pyrimidine X (50 mg, 0.19 mmol) in dioxane (5 ml) was added diisopropylethylamine (0.28 mmol, 47 μL) and a piperazine derivative (0.28 mmol). The reaction was stirred at 70° C. for 6 hours after which the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 2% CH3OH in CH2Cl2), yielding the pure title compounds which were characterized by their mass spectra as indicated below:The following compounds were synthesized according to this procedure:Example 190 Synthesis of 5-amino-2-(4-fluorophenyl)-7-(4-isobutylpiperazin-1-yl)-oxazolo[5,4-d]pyrimidineThis compound was obtained from 1-isobutyl-piperazine (32 mg);MS m/z (%): 371 ([M+H]+, 100).
32 mg With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 70℃; for 6h; 190 Example 190 Synthesis of 5-amino-2-(4-fluorophenyl)-7-(4-isobutylpiperazin-1-yl)-oxazolo[5,4-d]pyrimidine Examples 190-192 Synthesis of 5-amino-2-(4-fluorophenyl)-7-piperazin-1-yl-oxazolo[5,4-d]pyrimidine analogues General Procedure [0979] To a solution of 5-amino-7-chloro-2-(4-fluorophenyl)-oxazolo[5,4-d]pyrimidine X (50 mg, 0.19 mmol) in dioxane (5 ml) was added diisopropylethylamine (0.28 mmol, 47 μL) and a piperazine derivative (0.28 mmol). The reaction was stirred at 70° C. for 6 hours after which the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 2% CH3OH in CH2Cl2), yielding the pure title compounds which were characterized by their mass spectra as indicated below: [0980] The following compounds were synthesized according to this procedure: Example 190 Synthesis of 5-amino-2-(4-fluorophenyl)-7-(4-isobutylpiperazin-1-yl)-oxazolo[5,4-d]pyrimidine This compound was obtained from 1-isobutyl-piperazine (32 mg); MS m/z (%): 371 ([M+H]+, 100).
32 mg With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 70℃; for 6h; 190 Synthesis of 5-amino-2-(4-fluorophenyl)-7-(4-isobutylpiperazin-1-yl)-oxazolo[5,4-d]pyrimidine To a solution of 5-amino-7-chloro-2-(4-fluorophenyl)-oxazolo[5,4-d]pyrimidine X (50 mg, 0.19 mmol) in dioxane (5 ml) was added diisopropylethylamine (0.28 mmol, 47 μL) and a piperazine derivative (0.28 mmol). The reaction was stirred at 70° C. for 6 hours after which the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 2% CH3OH in CH2Cl2), yielding the pure title compounds which were characterized by their mass spectra as indicated below: [0996] The following compounds were synthesized according to this procedure: Example 190 Synthesis of 5-amino-2-(4-fluorophenyl)-7-(4-isobutylpiperazin-1-yl)-oxazolo[5,4-d]pyrimidine [0997] This compound was obtained from 1-isobutyl-piperazine (32 mg); [0998] MS m/z (%): 371 ([M+H]+, 100).
  • 11
  • [ 5308-28-1 ]
  • [ 1372616-37-9 ]
  • [ 1442655-83-5 ]
YieldReaction ConditionsOperation in experiment
74% With manganese(IV) oxide In dimethyl sulfoxide at 20℃; for 24h; RLZ analog (2e). A mixture of benzoxazinorifamycin 2d (5.5 mg, 0.005 mmol), l-(2- methylpropy piperazine (2.3 mg, 0.016 mmol; Oakwood Products Inc.), Mn02 (5 mg, 0.055 mmol) and DMSO (0.5 mL) was stirred at room temperature for 24 h and then filtered over Celite. The filtrate was concentrated and purified by preparative TLC, eluting with dichloromethane : methanol (90 : 10). The product band was processed to give 2e (4.6 mg, 74%) as a dark blue solid: HPLC 5.33 min (95.3% purity); MS (ES+) m/z 1189.5 (M+H)+; HRMS (MALDI) calcd for C49H61N3O13 [(M + H)+], 1189.6180; found 1189.6193.
  • 12
  • [ 5308-28-1 ]
  • [ 1610379-38-8 ]
  • [ 1610379-05-9 ]
YieldReaction ConditionsOperation in experiment
34% With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 6h; 5 2-(6-(4-Isobutylpiperazin-1-yl)pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one Example 5 2-(6-(4-Isobutylpiperazin-1-yl)pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one To a suspension of 2-(6-fluoropyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (0.108 g, 0.36 mmol) in N,N-dimethylformamide (1.5 mL) was added K2CO3 (0.15 g, 1.07 mmol) and 1-isobutyl-piperazine (88.94, 0.54 mmol). The resulting mixture was heated at 110° C. for 6 h. After that time N,N-dimethylacetamide (1.5 mL) was added and heating was continued for 20 h. After that time the reaction mixture was cooled to rt, diluted with ethyl acetate and filtered. The filtrate was concentrated under reduced pressure and the residue was washed with water, and dried under high vacuum. The product was purified by flash column chromatography (silica gel, 99:1 dichloromethane/methanol) to give 2-(6-(4-isobutylpiperazin-1-yl)pyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (0.052 g, 34%) as a yellow solid: mp 188-189° C.; 1H NMR (400 MHz, CDCl3) δ 10.33 (br s, 1H), 7.83 (d, J=7.42 Hz, 1H), 7.65 (dd, J=8.59, 7.42, 1H), 6.76-6.88 (m, 2H), 6.48 (d, J=2.34 Hz, 1H), 3.99 (s, 3H), 3.94 (s, 3H), 3.64 (t, J=4.88 Hz, 4H), 2.55 (t, J=4.88 Hz, 4H), 2.17 (d, J=7.42 Hz, 2H), 1.75-1.95 (m, 1H), 0.95 (d, J=6.64 Hz, 6H); ESI MS m/z 424 [M+H]+.
  • 13
  • [ 5308-28-1 ]
  • 2-bromo-N-[1-(1H-indol-3-yl)hexan-2-yl]-1,3-thiazole-5-carboxamide [ No CAS ]
  • N-(1-(1H-indol-3-yl)hexan-2-yl)-2-(4-isobutylpiperazin-1-yl)thiazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate In acetonitrile at 80℃; for 16h; 5 Example 5: N-(l-(lH-Indol-3-yl)hexan-2-yl)-2-(4-isobutylpiperazin-l-yl)thiazole-5- carboxamide. To a solution of N-(l-(lH-indol-3-yl)hexan-2-yl)-2-bromothiazole-5- carboxamide (0.20 g, 0.49 mmol) and 1-isobutylpiperazine (0.05 g, 0.54 mmol) in CH3CN (4.5 mL) was added K2C03 (0.20 g, 1.47 mmol) and the reaction mixture was heated at 80 °C for 16 h. The reaction mixture was concentrated in vacuo. The residue was diluted with H20 (10 mL) and extracted with 10% MeOH in DCM (10 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated in vacuo. The crude obtained was purified by column chromatography (silica 230-400 mesh, 0 to 10% MeOH in DCM) and then triturating with petroleum ether (6 mL), pentane (10 mL) and DCM (2 mL) to afford N-(l-(lH-indol-3- yl)hexan-2-yl)-2-(4-isobutylpiperazin-l-yl)thiazole-5-carboxamide (0.16 g, 69%) as an off-white solid. HPLC Purity: 97.4%. LC/MS (ESI) m/e [M+H]+/RT (min)/%: 468.00/3.33/99.52%. 1H NMR (400 MHz, DMSO- 6) δ 0.81 (t, = 6.8 Hz, 3H), 0.87 (d, = 6.4 Hz, 6H), 1.13-1.37 (m, 4H), 1.42-1.58 (m, 2H), 1.76-1.82 (m, 1H), 2.08 (d, = 6.8 Hz, 2H), 2.40-2.48 (m, 4H), 2.73- 2.95 (m, 2H), 3.42-3.48 (m, 4H), 4.10-4.18 (m, 1H), 6.92-6.99 (m, 1H), 7.04 (t, J = 7.3 Hz, 1H), 7.09 (brs, 1H), 7.31 (d, / = 8.3 Hz, 1H), 7.57 (d, = 7.3 Hz, 1H), 7.80 (s, 1H), 7.94 (d, = 8.8 Hz, 1H), 10.75 (brs, 1H).
  • 14
  • [ 5308-28-1 ]
  • [ 779345-37-8 ]
  • [ 1374636-03-9 ]
  • 15
  • [ 5308-28-1 ]
  • (2-(4-(trifluoromethyl) phenyl) acetyl)-L-tryptophan [ No CAS ]
  • (S)-N-(3-(1H-indol-3-yl)-1-(4-isobutylpiperazin-1-yl)-1-oxopropan-2-yl)-2-(4-(trifluoromethyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.6% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; General method for preparation of compounds 3a-3h,4a-4i, 5a-5k, and 6a-6d General procedure: Phenylacetic acid derivative (0.01 mol) or 3-(4-(trifluoromethyl)phenyl) propionic (0.01 mol) and L-tryptophanmethyl ester hydrochloride (0.01 mol) were added to anhydrousDCM; (100 mL), then Et3N (0.04 mol) was added, andthen the mixture was stirred for 10 min. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI)(0.012 mol) and 1-Hydroxybenzotriazole (HOBt)(0.7 mmol) were added and the mixture was stirred overnightat room temperature. Thereafter, the mixture waswashed with 0.1 N sodium hydroxide solution, 0.1 N HCl,and water. The organic layer was concentrated underreduced pressure to produce intermediates 1a-1i. Intermediate1 (5.0 mmol) was dissolved in methanol (20 mL) and heated to 60 oC. 1 N NaOH (10 mL) was added dropwiseand then stirred for 2 h at 60 oC. The reaction mixturewas cooled to room temperature, and the pH was adjusted to2-3 with HCl solution. The cake was filtered, washed withwater, and then dried under reduced pressure to obtainintermediates 2a-2i. Intermediate 2 (1.0 mmol) and variousamino derivatives (1.1 mmol) were added to anhydrousDCM (15 mL) and then Et3N (4.0 mmol), EDCI (1.2 mmol),and HOBt (0.07 mmol) were added. The mixture was stirredovernight at room temperature. Thereafter, the mixture waswashed with water, and then the crude product was crystallizedfrom methanol/water or purified by silica gel forcolumn chromatography (DCM/methanol) to obtain thetargeted product.
  • 16
  • [ 5308-28-1 ]
  • [ 64-18-6 ]
  • [ 160538-51-2 ]
  • 3-[4-(2-methylpropyl)piperazin-1-yl]-4-nitrobenzaldehyde formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% Stage #1: 1-isobutylpiperazine With triethylamine; cesium fluoride In acetonitrile at 20℃; for 0.333333h; Stage #2: 3-fluoro-4-nitro-benzaldehyde In acetonitrile at 20℃; Stage #3: formic acid In water; acetonitrile General procedure: General procedure 1 (13a-u). A solution of the corresponding amine (12a-u) (0.46 mmol, 1.3 Eq.), trimethylamine (1.06 mmol, 3 Eq.) and cesium fluoride (0.03 mmol, 0.1 Eq.) in ACN (1 ml) was stirred at room temperature for 20 min. To the reaction mixture was then added a solution of 3-fluoro-4-nitrobenzaldehyde (11) (0.35 mmol, 1 Eq.) in CAN (0.5 ml). The resulting reaction was then stirred at room temperature for 24 hours. After complete consumption of the starting materials - monitored by TLC (DCM/MeOH 19:1) and UHPLC-MS the mixture was filtered, and filtrate was evaporated under reduced pressure. Compound was purified by preparative HPLC. 3-(3-methoxyazetidin-1-yl)-4-nitrobenzaldehyde (13a). Compound 13a was synthesized using general procedure 1 and 3-azetidinyl methyl ether hydrochloride (12a). The crude reaction was purified using preparative HPLC to afford the desired compound as an orange amorphous solid (26 mg, 30% yield) with a purity of 98% by UHPLC-MS.
30% Stage #1: 1-isobutylpiperazine With triethylamine; cesium fluoride In acetonitrile at 20℃; for 0.333333h; Stage #2: 3-fluoro-4-nitro-benzaldehyde In acetonitrile at 20℃; Stage #3: formic acid In water; acetonitrile General procedure: General procedure 1 (13a-u). A solution of the corresponding amine (12a-u) (0.46 mmol, 1.3 Eq.), trimethylamine (1.06 mmol, 3 Eq.) and cesium fluoride (0.03 mmol, 0.1 Eq.) in ACN (1 ml) was stirred at room temperature for 20 min. To the reaction mixture was then added a solution of 3-fluoro-4-nitrobenzaldehyde (11) (0.35 mmol, 1 Eq.) in CAN (0.5 ml). The resulting reaction was then stirred at room temperature for 24 hours. After complete consumption of the starting materials - monitored by TLC (DCM/MeOH 19:1) and UHPLC-MS the mixture was filtered, and filtrate was evaporated under reduced pressure. Compound was purified by preparative HPLC. 3-(3-methoxyazetidin-1-yl)-4-nitrobenzaldehyde (13a). Compound 13a was synthesized using general procedure 1 and 3-azetidinyl methyl ether hydrochloride (12a). The crude reaction was purified using preparative HPLC to afford the desired compound as an orange amorphous solid (26 mg, 30% yield) with a purity of 98% by UHPLC-MS.
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