57561-39-4 N-Boc-N-methyl-aminothanol

Rau kev daws ntawm 2-(methylamino) ethanol (500 mg, 0.53 ml, 6.66 mmol) hauv CH2Cl2 (20 ml) tau ntxiv Boc2O (1.48 g, 6.79 mmol), tom qab ntawd nplawm hauv chav sov li 1 teev.Cov tshuaj tiv thaiv tau muab rho tawm nrog brine thiab CH2Cl2.Cov txheej txheem organic li no tau qhuav dhau MgSO4 thiab lim.Tom qab ntawd, cov filtrate yog concentrated nyob rau hauv vacuo kom tau cov khoom compound (colourless oil, quantitative);1H NMR (200 MHz, CDCl3) delta 3.74 (q, J = 10.5, 5.2 Hz, 2H) 3.25 (t, J = 5.2 Hz, 2H) 2.91 (s, 3H) 1.45 (s, 9H);huab hwm coj spectrum m/e (kwv yees siv) 144 (20) 102 (24) 57 (70) 44 (100).
Piv txwv 38;N1-(3-Fluoro-4-(2-(1-(2-(methylamino)ethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3 -(2-methoxyphenyl)malonamide (96);Kauj Ruam 1: tert-Butyl 2-hydroxyethyl (methyl)carbamate (97) (J. Med. Chem., 1999, 42, 11, 2008) Rau kev daws ntawm 2-(methylamino) ethanol (5.0 g, 67 mmol) hauv THF (50 ml) ntawm RT tau ntxiv Boc2O (15.7 g, 72 mmol) thiab cov tshuaj tiv thaiv sib xyaw yog nplawm ntawm RT rau 4 teev.Cov tshuaj tiv thaiv sib tov yog concentrated rau dryness thiab lub npe compound 97 tau siv ncaj qha rau hauv cov kauj ruam tom ntej uas tsis muaj purification ntxiv (11.74 g, 100% tawm los).MS (m / z): 176.2 (M + H).
Kev npaj ntawm l-2-[4-Bromo-2-(4-oxo-2-ftiotaioxo1hiazolidin-5-ylidenemefliyl)phenoxy]efliyl-3-efliyl-l- methylurea(Compoiotamd 161) Kauj Ruam 1: Synthesis ntawm t-butyl2- hydroxyethylmethylcarbamate;Rau kev daws ntawm 2-(methylamino) ethanol (500 mg, 0.53 ml, 6.66 mmol) hauv CH2Cl2 (20 ml) tau ntxiv BoC2O (1.48 g, 6.79 mmol), tom qab ntawd nplawm ntawm chav tsev kub rau 1 teev.Cov tshuaj tiv thaiv tau muab rho tawm nrog brine thiab CH2Cl2.Cov txheej txheem organic li no tau qhuav dhau MgSO4 thiab lim.Tom qab ntawd, cov filtrate yog concentrated nyob rau hauv vacuo kom tau cov khoom compound (colourless oil, quantitative); 1HNMR (200 MHz, CDCl3) delta 3.74 (q, J = 10.5, 5.2 Hz, 2H) 3.25 (t, J = 5.2 Hz, 2H) 2.91 (s, 3H) 1.45 (s, 9H);huab hwm coj spectrum m/e (kwv yees siv) 144 (20) 102 (24) 57 (70) 44 (100).
2-(methylamino) ethanol (90.1 g, 1.2 mol) tau yaj hauv 1.2 L ntawm methylene chloride, thiab BoC2O (218 g, 1 mol) tau maj mam ntxiv rau qhov ntawd thaum nplawm ntawm 00C, tom qab ntawd hauv chav sov li 3 teev.Cov tshuaj tiv thaiv sib xyaw tau ua ntu zus nrog 700 mL ntawm cov tshuaj aqueous ntawm saturated ammonium chloride, thiab 300 mL dej.Cov sib tov ntxuav yog dehydrated siv anhydrous sodium sulfate thiab concentrated nyob rau hauv ib tug txo lub siab, kom tau cov compound (a) (175 g, 1 mol, 100%) raws li ib tug roj uas tsis muaj xim.TLC: Rf = 0.5 (50% EtOAc nyob rau hauv Hex) pom nrog Ce-Mo stain1H NMR (600MHz, CDCl3) delta 1.47 (s, 9H), 2.88 (br s, IH), 3.41 (br s, 2H), 3.76 (br s, 2H).
90.1 g (1.2 mol) ntawm 2-(methylamino) ethanol tau yaj nyob rau hauv 1.2 L ntawm methylene chloride, 218 g (1 mol) ntawm Boc2O tau maj mam ntxiv rau qhov ntawd thaum cov tshuaj tov tau nplawm ntawm 0C, thiab cov txiaj ntsig daws tau nplawm ntawm chav sov rau 3 teev.Cov tshuaj tiv thaiv sib tov tau ua ntu zus nrog 700 mL ntawm aqueous saturated ammonium chloride tov thiab 300 mL dej, lub cev qhuav dej siv anhydrous sodium sulfate, thiab tom qab ntawd concentrated nyob rau hauv lub siab txo kom tau 175 g (1 mol) ntawm ib tug achromic roj compound tiv thaiv los ntawm lub Boc pawg (yield: 100%).[0140] 1H NMR (600MHz, CDCl3) delta 7.84 (br s, 2H), 7.76 (br s, 2H), 4.34 (d, J = 15.0 Hz, 2H), 3.63 (br s, 2H), 3.04 (d , J = 15.0 Hz, 3H), 1.46 (d, J = 16.2 Hz, 9H) [0141] 90 g (0.514 mol) ntawm cov khoom tau tau yaj hauv 1.5 L ntawm tetrahydrofuran, 88.0 g (539 mol) ntawm N- hydroxyphthalimide thiab 141 g (0.539 mol) ntawm triphenylphosphine tau ntxiv rau ntawd, 106 mL (0.539 mol) ntawm diisopropyl azodicarboxylate tau maj mam ntxiv rau ntawd thaum nplawm cov tshuaj daws ntawm 0C, thiab cov txiaj ntsig daws tau nplawm rau 3 teev thaum qhov kub ntawm qhov ntawd tau nce. mus rau chav kub.Tom qab cov concentration ntawm cov tshuaj tiv thaiv sib tov nyob rau hauv lub siab txo, 600 mL ntawm isopropylether tau ntxiv rau qhov ntawd, cov kev daws teeb meem tau nplawm ntawm 0C rau 1 teev, thiab cov khoom dawb-hom triphenylphosphine oxide tau lim.Cov khoom raug ntxuav nrog 200 mL ntawm isopropylether txias rau 0C thiab sau nrog thawj filtrate, thiab lub resulting filtrate yog concentrated nyob rau hauv lub siab txo kom tau 198 g ntawm ib tug sib tov ntawm Compound XX thiab diisopropyl hydrazodicarboxylate nyob rau hauv ib tug sib piv ntawm 10 mus rau 15%. (Yield: 120%).[0142] 1H NMR (600MHz, CDCl3) delta 7.84 (br s, 2H), 7.76 (br s, 2H), 4.34 (d, J = 15.0 Hz, 2H), 3.63 (br s, 2H), 3.04 (d J = 15.0 Hz, 3H), 1.46 (d, J = 16.2 Hz, 9H)