Nnc-21-0136 → N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-bromoadenosine

Participants

Reaction Steps

The title compound was prepared according to general method A as described above in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]benzothiazole hydrochloride (prepared as indicated in Example 5) (1.07 g, 3.6 mmol) with 2-bromo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-9H-purine (see WO 93/08206; Bioorganic and Medicinal Chemistry Letters, 1993, 3, 2661-2666) (1.48 g, 3.0 mmol) followed by deacylation of the purified 2',3',5'-tri-O-acetyl-2-bromo-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-bromoadenosine (0.20 g, 14%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 3.50-3.77 (4H, m, H-5'a, and H-5'b and --CH2 --), 3.94 (1H, d, H-4'), 4.12 (1 H, d, H-3'), 4.51 (1H, q, H-2'), 4.70 1H, m, --CHCH3), 5.05 (1H, t, 5'-OH), 5.22, 5.49 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 7.36, 7.46 (2H, 2t, Ar-H), 7.86, 7.99 (2H, 2d, Ar-H), 8.40 (1H, s, H-8). HPLC retention time 6.74 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence