ChemicalBook CAS DataBase List ZM 241385

ZM 241385 synthesis

7synthesis methods

Product Name:ZM 241385
CAS Number:139180-30-6
Molecular formula:C16H15N7O2
Molecular Weight:337.34

51-67-2
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2-(furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine

139181-28-5
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139180-30-6
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$25.00/1mg

Yield:139180-30-6 33%

Reaction Conditions:

in acetonitrile at 20;

Steps:

4-(2-((7-Amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol (5) (ZM 241385)
Tyramine (490 mg, 3.75 mmol) was added to a suspension of 2-(furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine (18) (250 mg, 892 μmol) in acetonitrile (25 mL). The reaction mixture was stirred overnight at room temperature. After 22 h the solvent was evaporated, the residue was adsorbed on Celite and purified by column chromatography (dichloromethane: methanol 25:75). The collected fractions with product were evaporated to dryness and recrystallised from ethyl acetate. The title compound 5 (100 mg, 33%) was obtained as a white solid, mp: 229-231 °C (lit.⁶ 225-227 °C). ¹H NMR (400 MHz, d₆-DMSO, 353 K) δ 8.91 (s, 1H), 7.92 (br s, 2H), 7.79 (m, 1H), 7.14 (br t, 1H), 7.04 (m, 3H), 6.71 (m, 2H), 6.64 (dd, J = 3.3, 1.8 Hz, 1H), 3.49 (m, 2H), 2.78 (m, 2H). ¹³C NMR (101 MHz, d₆-DMSO) δ 161.1 (C), 159.0 (C), 155.9 (C), 155.4 (C), 150.1 (C), 146.1 (C), 144.1 (CH), 129.1 (CH), 115.0 (CH), 111.4 (CH), 111.2 (CH), 42.4 (CH₂), 33.9 (CH₂). HRMS (C₁₆H₁₅N₇O₂): calc’d 338.1360 [M+H]⁺, found 338.1353. HPLC: t_R 7.34 min, 98% (214 nm), 97% (254 nm).

References:

J?rg, Manuela;Shonberg, Jeremy;Mak, Frankie S.;Miller, Neil D.;Yuriev, Elizabeth;Scammells, Peter J.;Capuano, Ben [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 11,p. 3427 - 3433] Location in patent:supporting information

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