2-Thiophenethiol → HCID 22858277, compound

HRID 2292612Notes

Reaction equation

HRID 2292612 reaction equation
Cl.N[C@H](C)CSC1SC=CC=1.SC1SC=CC=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:83]2[N:82]=[C:81]([Cl:84])[N:80]=[C:69]([NH:70][C@H:71]([CH3:79])[CH2:72][S:73][C:74]3[S:75][CH:76]=[CH:77][CH:78]=3)[C:68]=2[N:67]=[CH:66]1)(=O)C.C[O-].[Na+]>CO>[Cl:84][C:81]1[N:80]=[C:69]([NH:70][C@H:71]([CH3:79])[CH2:72][S:73][C:74]2[S:75][CH:76]=[CH:77][CH:78]=2)[C:68]2[N:67]=[CH:66][N:65]([C:83]=2[N:82]=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]

Participants

7

Reactant 5

HCID 5226742-ThiophenethiolHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 10942334Sodium MethoxideHCID 22858302HCID 22858302, compoundHCID 67771709HCID 67771709, compound

Product 1

HCID 22858277HCID 22858277, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared according to method A as described in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]thiophene hydrochloride [prepared by a Mitsunobu reaction as described in Example 1 using 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (7.53 g, 43 mmol) and 2-mercaptothiophene (5.00 g, 43 mmol) followed by acidic hydrolysis] (0.63 g, 3.0 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.12 g, 2.5 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-2-chloro-N-[(R)-1-(2-thienyl)thio-2-propyl]adenosine using sodium methoxide in methanol to provide the title 2-chloro-N-[(R)-1-(2-thienyl)thio-2-propyl]adenosine (0.95 g, 82%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ1.26 (3H, d, --CHCH3), 2.95-3.18 (2H, ABX, --CH2 --S--), 3.55 and 3.61 (2H, ABX, H-5'a and H-5'b ), 3.95 (1H, q, H-4), 4.14 (1H, t, H-3'), 4.44 (1H, m, --CH--CH3), 4.54 (1H, t, H-2'), 5.84 (1H, d, H-1'), 7.03 (1H, t, Ar--H), 7.23, 7.61 (2H, 2d, Ar--H), 8.38 (1H, d, --NH), 8.42 (1H, s, H-2). HPLC retention time 19.5 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Workup

  1. customThe title compound was prepared
  2. customprepared by a Mitsunobu reaction

Sources & evidence

ORD record
ord-748c01a0d729418c9c836855079fd2f1
Source dataset
uspto-grants-1997_11
Patent number
US05683989

Reaction notes

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