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ChemicalBook CAS DataBase List Momelotinib
1056634-68-4

Momelotinib synthesis

13synthesis methods

Momelotinib (CYT387) is an ATP-competitive inhibitor of JAK1/JAK2 with IC50 of 11 nM/18 nM, ~10-fold selectivity versus JAK3. Phase 3.  It was prepared from 5-1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride with benzotriazol-1-ol by stirring DMF for overnight at room temperature.

945749-71-3 Synthesis
4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoic acid

945749-71-3
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6011-14-9 Synthesis
Aminoacetonitrile hydrochloride

6011-14-9
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Yield:1056634-68-4 90%

Reaction Conditions:

with benzotriazol-1-ol;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;triethylamine in N,N-dimethyl-formamide at 20;

Steps:

Synthesis of N-(cyanomethyl)-4-{2-[(4-morpholinophenyl)amino]pyrimidin-4-yl}benzamide (momelotinib)
Et3N (4.1 mL, 30 mmol) was added to a mixture of compound 6(1.88 g, 5.0 mmol) in DMF (20 mL). Then aminoacetonitrile hydrochloride (0.93 g, 10 mmol) was added followed by N-hydroxybenzotriazole (HOBt, 0.81 g, 6.0 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 g, 6.0 mmol). The mixture was stirred overnight at room temperature. After removing the solvents under reduced pressure, the residue was dissolved in CH2Cl2 (100 mL) and washed with NaHCO3 aqueous solution. The organic phase was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by column chromatography on 200-300 mesh silica with EtOAc to afford momelotinib as: Yellow solid; yield 1.86 g (90%); m.p. 232-234 °C (lit.14 238-243 °C); IR: 3365, 3282, 1660, 1596, 1576, 1512, 1456, 1232 cm-1. Anal. calcd for C23H22N6O2: C, 66.65; H, 5.35; N, 20.28; found: C, 66.78; H, 5.49; N, 20.39%. ESI-MS: 415.1 [M + H]+, 437.1 [M + Na]+, 413.2 [M - H]-; 1H NMR (300 MHz, DMSO-d6): δ 9.47 (s, 1H), 9.32 (t, J = 5.4 Hz, 1H), 8.54 (d, J = 5.1 Hz, 1H), 8.27 (d,J = 8.1 Hz, 2H), 8.03 (d, J = 8.1 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 7.40 (d, J = 5.1 Hz, 1H), 6.94 (d, J = 8.7 Hz, 2H), 4.35 (d, J = 5.1 Hz, 2H), 3.74-3.77 (m, 4H), 3.04-3.07 (m, 4H); 13C NMR (75 MHz, DMSO-d6): δ 166.1, 162.4, 160.3, 159.2, 146.2, 139.9, 134.5, 132.8, 127.8, 126.9, 120.3, 117.5, 115.6, 107.6, 66.1, 49.2, 27.7.

References:

Sun, Tong;Xu, Jiaojiao;Ji, Min;Wang, Peng [Journal of Chemical Research,2016,vol. 40,# 8,p. 511 - 513]

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