Reacción #820088

ord-02c9a549ddd54261b6b39bf76d44e4e9

Ecuación de reacción

C#CCC1CCN(C(=O)Oc2ccc(Cl)cc2)CC1
4-chlorophenyl 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(Cl)cc3)CC2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
2-{3-[1-((4-Chloro)phenoxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Reactantes

C#CCC1CCN(C(=O)Oc2ccc(Cl)cc2)CC1
4-chlorophenyl 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=7.3 min.

Procedimiento

Batch: AB-10-015. 4-chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-107 (0.624 g, 2.247 mmol) was added to a solution of 2-iodoadenosine (0.656 g, 1.669 mmol) according to general procedure 2. Yield: 0.445 g, 49%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 7.37-7.07 (2×m, 4H), 5.93 (d, 1H), 4.71 (m, 2H), 4.31-4.17 (2×m, 3H), 3.91-3.75 (2×d, 2H), 3.07-2.93 (2×bt, 4H), 2.48 (d, 5H), 1.97-1.40 (2×m, 5H). m/z MH+=543.09. HPLC rt=7.3 min.

Fuente

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