Reacción #820090

ord-2bab6b391895411fa54edbdbcfd25609

Ecuación de reacción

C#CCC1CCN(C(=O)Oc2ccc(C)cc2)CC1
4-methylphenyl 4-(prop-2-ynyl)piperidine-1-carboxylate
Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-iodoadenosine
→
Cc1ccc(OC(=O)N2CCC(CC#Cc3nc(N)c4ncn([C@@H]5O[C@H](CO)[C@@H](O)[C@H]5O)c4n3)CC2)cc1
2-{3-[1-((4-Methyl)phenoxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Reactantes

—
JR28-105
C#CCC1CCN(C(=O)Oc2ccc(C)cc2)CC1
4-methylphenyl 4-(prop-2-ynyl)piperidine-1-carboxylate
Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-iodoadenosine

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroHPLC rt=6.8 min.

Procedimiento

Batch: AB-10-019. 4-methylphenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-105 (0.548 g, 2.130 mmol) was added to a solution of 2-iodoadenosine (0.629 g, 1.600 mmol) according to general procedure 2. Yield: 0.236 g, 28%. 1H NMR (CD3OD) δ 8.29 (s, 1H), 7.14-6.92 (2×m, 4H), 5.95 (d, 1H), 4.75 (m, 2H), 4.34-4.16 (2×m, 3H), 3.91-3.71 (2×d, 2H), 3.10-2.90 (2×bt, 4H), 2.28 (s, 3H), 2.43 (d, 5H), 1.92-1.41 (2×m, 5H). m/Z MH+=523.16. HPLC rt=6.8 min.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07589076B2uspto-grants-2009_09