Reacción #820094

ord-817e30ee7b3340beb4d2e4ec49537faf

Ecuación de reacción

C#CCC1CCN(C(=O)Oc2ccc(F)c(F)c2)CC1
3,4-Difluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate
Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-iodoadenosine
→
Nc1nc(C#CCC2CCN(C(=O)Oc3ccc(F)c(F)c3)CC2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-{3-[1-((3,4-Difluoro)phenoxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Reactantes

C#CCC1CCN(C(=O)Oc2ccc(F)c(F)c2)CC1
3,4-Difluorophenyl 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=9.1 min.

Procedimiento

3,4-Difluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate (1.830 g, 6.55 mmol) was added to a solution of 2-iodoadenosine (0.611 g, 1.554 mmol) according to general procedure 2: yield 201 mg, 24%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 7.25 (m, 1H), 7.12 (m, 1H), 6.96-6.89 (m, 1H), 5.93 (d, 1H, J=6.5 Hz), 4.71 (dd, 1H, J=5.1 Hz, J=6.4 Hz), 4.35-4.24 (m, 2H), 4.23-4.13 (m, 2H), 3.89 (dd, 1H, J=2.3 Hz, J=12.6 Hz), 3.74 (dd, 1H, J=2.5, J=12.6 Hz), 3.05, 2.91 (2×br t, 2H), 2.46 (d, 2H, J=6.2 Hz), 2.01-1.79, 1.52-1.27 (2×m, 5H). LRMS ESI (M+H+) 545.2. HPLC rt=9.1 min.

Fuente

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