Réaction #44343

ord-725c15caf0dc4b3d8c11ea508702542d

Équation de réaction

CN
methylamine
CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)nc(C#CCC4CCC(C(=O)OC)CC4)nc32)[C@H](O)[C@@H]1O
ATL146e
→
CCNC(=O)C1OC(n2cnc3c(N)nc(C#CCC4CCC(C(=O)NC)CC4)nc32)C(O)C1O
JR3065
Rendement 48.0%
CCNC(=O)C1OC(n2cnc3c(N)nc(C#CCC4CCC(C(=O)NC)CC4)nc32)C(O)C1O
5-{6-Amino-2-[3-(4-methylcarbamoyl-cyclohexyl)-prop-1-ynyl]-purin-9-yl}-3,4-dihydroxytetrahydrofuran-2-carboxylic acid ethylamide
Rendement 48.0%

Réactifs

CN
methylamine
CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)nc(C#CCC4CCC(C(=O)OC)CC4)nc32)[C@H](O)[C@@H]1O
ATL146e

Réactifs

Aucun

Solvants

CO
methanol

Conditions de réaction

Température
70°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe flask was sealed
  2. 2
    TempératureThe vessel was cooled to 0° C.
  3. 3
    Autrethe solvent was removed in vacuo

Mode opératoire

To a sealed tube containing 10 mL 2.0 M methylamine in methanol was added 16.5 mg (0.03 mmol) of ATL146e. The flask was sealed and allowed to stir at 70° C. for 120 hours. The vessel was cooled to 0° C., opened, and the solvent was removed in vacuo to yield 8.0 mg (48%) of JR3065 as a white solid after the residue was purified by RP-HPLC. 1H NMR (CD3OD-d4) δ. 13C NMR (CD3OD-d4) δ. APCI m/z (rel intensity) 486.3 (MH+, 100), 313.4 (35).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07737127B2uspto-grants-2010_06