2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 22858286, compound

HRID 375169Notes

Reaction equation

HRID 375169 reaction equation
Cl.Cl.Cl.N[C@H](C)CNC1SC2C=CC=CC=2N=1.C(O[C@@H]1[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1N1C=NC2C1=NC(Cl)=NC=2Cl)(=O)C.C([O:50][C@@H:51]1[C@H:55]([O:56]C(=O)C)[C@@H:54]([CH2:60][O:61]C(=O)C)[O:53][C@H:52]1[N:65]1[C:87]2[N:86]=[C:85]([Cl:88])[N:84]=[C:69]([NH:70][C@H:71]([CH3:83])[CH2:72][NH:73][C:74]3[S:75][C:76]4[CH:82]=[CH:81][CH:80]=[CH:79][C:77]=4[N:78]=3)[C:68]=2[N:67]=[CH:66]1)(=O)C.C[O-].[Na+]>CO>[S:75]1[C:76]2[CH:82]=[CH:81][CH:80]=[CH:79][C:77]=2[N:78]=[C:74]1[NH:73][CH2:72][C@H:71]([NH:70][C:69]1[C:68]2[N:67]=[CH:66][N:65]([C:87]=2[N:86]=[C:85]([Cl:88])[N:84]=1)[C@@H:52]1[O:53][C@H:54]([CH2:60][OH:61])[C@@H:55]([OH:56])[C@H:51]1[OH:50])[CH3:83]

Participants

6

Reactant 4

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 10942334Sodium MethoxideHCID 22858310HCID 22858310, compoundHCID 86749212HCID 86749212, compound

Product 1

HCID 22858286HCID 22858286, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[(R)-(2-Amino-1-propyl)amino]benzothiazole trihydrochloride (0.065 g, 70%), m.p. 226-226° C., was subsequently obtained by hydrolysis in a mixture of 6N hydrochloric acid and ethyl acetate (2 ml), the procedure described in Example 1. This 2-[(R)-(2-amino-1-propyl)amino]benzothiazole trihydrochloride (0.06 g, 0. 19 mmol) was reacted with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-di-chloro-9H-purine (0.127 g, 1.2 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(2-benzothiazolyl)amino-2-propyl]-2-chloroadenosine using sodium methoxide in methanol (to remove the 2' and 3'-acetyl groups) followed by ethylamine in ethanol, which provided the title N-[(R)-1-(2-benzothiazolyl)amino-2-propyl]-2-chloroadenosine (0.027 g, 29%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.25 (3H, d, --CHCH3), 3.52-3.70 (4H, m, H-5'a , H-5'b and --CH2 --), 3.94 (1H, q, H-4'), 4.12 (1H, q, H-3'), 4.52 (1H, q, H-2'), 4.53 -4.62 (1H, m, --CHCH3), 5.07 (1H, t, 5'-OH), 5.22, 5.48 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.01, 7.22 (2H, 2t, Ar-H), 7.43, 7.66 (2H, 2d, Ar-H), 8.14 (1H, t, N--H), 8.41 (1H, s, H-8), 8.44 (1H, d, N--H). HPLC retention time 10.7 min [gradient elution, 20-80% acetonitrile/water (containing 0. 1% TFA)].

Workup

  1. customto remove the 2' and 3'-acetyl groups)

Sources & evidence

ORD record
ord-37d9ae322a9344b6a5169617e68cd7d1
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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