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With methanol; sodium cyanoborohydride In tetrahydrofuran at 65℃; for 16 h;
Methyl 4-acetylbenzoate (1.07 g, 6 mmol), methylamine (33 percent in EtOH, 4.5 mL), methylamine hydrochloride (1.62 g, 24.0 mmol) and sodium cyanoborohydride (0.56 g, 9.0 mmol) were dissolved in a mixture of THF (12 mL) and Methanol (7 mL) and the reaction stirred at 65 0C for 16 h. The reaction was concentrated in vacuo and the residue redissolved in DCM (20 mL) and washed with water (20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo to afford the title compound, which was used without further purification. Yield: 0.86 g, 75 percent LCMS method B: rt 0.98 min, 89 percent; m/z 194.05 (MH+, 100 percent).
To 5 mL of tetrahydrofuran solution containing 177.8 mg of lithium aluminum hydride, 3 mL of tetrahydrofuran solution containing 245 mg of <strong>[80051-07-6]methyl 4-(1-aminoethyl)benzoate</strong> (synthesized according to a method disclosed in page 115 in Pamphlet of International Publication WO 03/024,955) was added, and then stirred for 1 hour. Thereto, sodium sulfate decahydrate was added until there are no bubbles, and stirred overnight at room temperature. The mixture was filtered through celite, the filtrate was concentrated under reduced pressure, and 195 mg of [4-(1-aminoethyl)phenyl]methanol [115-1] was obtained as a colorless oily product.
With methanol; sodium cyanoborohydride; In tetrahydrofuran; at 65℃; for 16.0h;
Methyl 4-acetylbenzoate (1.07 g, 6 mmol), methylamine (33 % in EtOH, 4.5 mL), methylamine hydrochloride (1.62 g, 24.0 mmol) and sodium cyanoborohydride (0.56 g, 9.0 mmol) were dissolved in a mixture of THF (12 mL) and Methanol (7 mL) and the reaction stirred at 65 0C for 16 h. The reaction was concentrated in vacuo and the residue redissolved in DCM (20 mL) and washed with water (20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo to afford the title compound, which was used without further purification. Yield: 0.86 g, 75 % LCMS method B: rt 0.98 min, 89 %; m/z 194.05 (MH+, 100 %).
With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16.0h;
Methyl 4-(l-aminoethyl)benzoate (0.86 g, 4.5 mmol), di-tert-butyl-dicarbonate (1.07 g, 4.91 mmol) and DIPEA were dissolved in DCM (8 rnL) prior to addition of DMAP (60 mg, 0.45 mmol). The reaction was stirred at ambient temperature for 16 h, diluted with DCM (10 mL) and washed with aqueous citric acid solution (10 % w/v, 20 mL) and saturated aqueous NaHCOs solution (20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo to afford the title compound, which was used without further purification. Yield: 1.14 g, 86 %
With hydrogen; In methanol; at 20℃; under 2585.81 Torr; for 4.0h;Inert atmosphere;
To a solution of methyl 4-(1-(hydroxyimino)ethyl)benzoate (800 mg, 4.14 mmol) in methanol (30 mL) was added Raney-Nickel (700 mg). The reaction mixture was stirred under hydrogen (50 psi) at rt for 4 hrs. On completion, the mixture was filtered. The filtrate was concentrated in vacuo to give the title compound. ?H NMR (4001V11{z, DMS 0-cl6) = 7.90 (d, J = 8.4 Hz, 2H), 7.52 (d, J= 8.0 Hz, 2H), 4.06 (q, J= 6.8 Hz, 1H), 3.84 (s, 3H), 1.25 (d, J 6.8 Hz, 3H).
(±) methyl 4-(1-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)ethyl)benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
61%
With triethylamine; In dichloromethane; at 0 - 20℃; for 5.0h;
General procedure: To a stirred solution ofthe corresponding amine (2 mmol) in anhydrous CH2Cl2 containing drytriethylamine (5 mmol) a solution of 3 or 15a-c (2.5 mmol) in anhydrousCH2Cl2 (5 mL) was added dropwise over 15 min at 0 C. Afterstirred for another 5 h at room temperature, water was added, and themixture was extracted with CH2Cl2. The combined organic phase wasdried (Na2SO4) and filtered to obtain the crude products, which werepurified by column chromatography using silica gel and a CH2Cl2/MeOH mixture. (CH2Cl2: MeOH=100:1)
General procedure: To a stirred solution of ortho-benzoquinone (0.825 mmol, 1.0equiv) in acetonitrile (4.0 mL), was added dropwise a solution ofprimary amine (0.825 mmol, 1.0 equiv) in acetonitrile (4.25 mL)over 5 min under an argon atmosphere. The deep green colouredsolution was stirred at room temperature for 2e8 h. Aftercompletion of the reaction, as indicated by TLC, the reactionmixture was cooled to 0C. To this, triethylamine (0.34 mL,2.48 mmol, 3 equiv) and iodine granules (0.419 g, 1.65 mmol, 2 eq),were added. The resulting mixture was stirred vigorously for10e60 min under argon atmosphere. Upon completion, the reac-tion mixture was diluted with water and extracted with EtOAc(3 5 mL). The combined organic layer was washed with aqueoussaturated sodium thiosulfate (1 10 mL) and brine (2 10 mL),respectively, dried over Na2SO4, ltered, and concentrated in vacuo.The crude residue was puried by silica gel column chromatog-raphy eluting with pentane:EtOAc (95:5e80:20 v:v) to afford thedesired benzo[1,4]oxazine product.
methyl 4-[1-[(2,5,6- trimethylpyrimidin-4-yl)amino]ethyl]benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
41.91%
With triethylamine In iso-butanol at 120℃; for 12h;
54
A mixture of methyl 4-(l-aminoethyl)benzoate (200.00 mg, 1.12 mmol, 1 eq), 4-chloro-2, 5, 6-trimethyl-pyrimidine (227.21 mg, 1.45 mmol, 1.3 eq) and Et3N (338.78 mg, 3.35 mmol, 465.99 pL, 3 eq) in butan-2-ol (5 mL) was stirred at 120°C for 12 hrs. The mixture was concentrated in reduced pressure to give a residue. The residue was purified by prep-TLC (SiCh, Petroleum ether/Ethyl acetate = 0/1) to give methyl 4-[l-[(2,5,6- trimethylpyrimidin-4-yl)amino]ethyl]benzoate (140 mg, 467.65 umol, 41.91% yield) as a light brown oil. ESI [M+H] = 300.1.
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