Nnc-21-0136 → 2-amino-N-[(R)-1-(2-benzothiazolyl)thio2-propyl]adenosine

HRID 375155Notes

Reaction equation

HRID 375155 reaction equation
ClC1N=C(N[C@H](C)CSC2SC3C=CC=CC=3N=2)C2N=CN(C=2N=1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.NC1N=C2C(N=CN2[C@@H]2O[C@H](COC(=O)C)[C@@H](OC(=O)C)[C@H]2OC(=O)C)=C(Cl)N=1.C([O:66][C@@H:67]1[C@H:71]([O:72]C(=O)C)[C@@H:70]([CH2:76][O:77]C(=O)C)[O:69][C@H:68]1[N:81]1[C:103]2[N:102]=[C:101]([NH2:104])[N:100]=[C:85]([NH:86][C@H:87]([CH3:99])[CH2:88][S:89][C:90]3[S:91][C:92]4[CH:98]=[CH:97][CH:96]=[CH:95][C:93]=4[N:94]=3)[C:84]=2[N:83]=[CH:82]1)(=O)C.C[O-].[Na+]>CO>[NH2:104][C:101]1[N:100]=[C:85]([NH:86][C@H:87]([CH3:99])[CH2:88][S:89][C:90]2[S:91][C:92]3[CH:98]=[CH:97][CH:96]=[CH:95][C:93]=3[N:94]=2)[C:84]2[N:83]=[CH:82][N:81]([C:103]=2[N:102]=1)[C@@H:68]1[O:69][C@H:70]([CH2:76][OH:77])[C@@H:71]([OH:72])[C@H:67]1[OH:66]

Participants

6

Reactant 4

HCID 9936084Nnc-21-0136HCID 10788628(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetateHCID 10942334Sodium MethoxideHCID 228582982',3',5'-tri-O-acetyl-2-amino-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine

Product 1

HCID 228583192-amino-N-[(R)-1-(2-benzothiazolyl)thio2-propyl]adenosineYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 described in Example 5) (7.13 g, 24 mmol) with 2-amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-9H-purine (Nucleic Acid Chemistry, Townsend L. B. and Tipson, R. S., eds., John Wiley and Sons Inc., 1986, 3, 144) (8.56 g, 20 mmol) followed by deacylation of a portion of the purified 2',3',5'-tri-O-acetyl-2-amino-N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title 2-amino-N-[(R)-1-(2-benzothiazolyl)thio2-propyl]adenosine (0.71 g, 19%) as a foam (following column chromatography) 1H NMR (DMSO-d6) δ 1.34 (3H, d, --CHCH3), 3.50-3.73 (4H, m, H-5'a and H-5'b and --CH2 --), 3.90 (1H, q, H- 4'), 4.10 (1H, d, H-3'), 4.51 (1H, q, H-2'), 5.11, 5.37 (2H, 2d, 2'- and 3'-OH), 5.40 (1H, t, 5'-OH), 5.73 (1H, d, H-1'), 5.79 (1H, br, --NH2), 7.36, 7.47 (2H, 2t, Ar-H), 7.92 (1H, s, H-8), 8.0 (1H, d, N--H). HPLC retention time 13.5 min [gradient elution, 20-80% acetonitrile/water (containing 0. 1% TFA)].

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c9d60e9f2bd74fe28c811a6396a54d95
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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