2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 22858285, compound

HRID 375164Notes

Reaction equation

HRID 375164 reaction equation
Cl.N[C@H](C)CSC1NC2C=CC=CC=2N=1.SC1NC2C=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:58][C@@H:59]1[C@H:63]([O:64]C(=O)C)[C@@H:62]([CH2:68][O:69]C(=O)C)[O:61][C@H:60]1[N:73]1[C:95]2[N:94]=[C:93]([Cl:96])[N:92]=[C:77]([NH:78][C@H:79]([CH3:91])[CH2:80][S:81][C:82]3[NH:83][C:84]4[CH:90]=[CH:89][CH:88]=[CH:87][C:85]=4[N:86]=3)[C:76]=2[N:75]=[CH:74]1)(=O)C>N.ClCCl>[N:83]1[C:84]2[CH:90]=[CH:89][CH:88]=[CH:87][C:85]=2[NH:86][C:82]=1[S:81][CH2:80][C@H:79]([NH:78][C:77]1[C:76]2[N:75]=[CH:74][N:73]([C:95]=2[N:94]=[C:93]([Cl:96])[N:92]=1)[C@@H:60]1[O:61][C@H:62]([CH2:68][OH:69])[C@@H:63]([OH:64])[C@H:59]1[OH:58])[CH3:91]

Participants

7

Reactant 4

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 22858309HCID 22858309, compoundHCID 22858326HCID 22858326, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 22858285HCID 22858285, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to method A as described in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]benzimidazole hydrochloride [prepared by a Mitsunobu reaction as described in Example 1 using 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (1.75 g, 10 mmol) and 2-mercaptobenzimidazole (1.5 g, 10 mmol) followed by acidic hydrolysis] (0.63 g, 2.20 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.0 g, 2.2 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(2-benzimidazolyl)thio-2-propyl]-2-chloroadenosine in methanolic ammonia (200 ml) (previously saturated at -10° C.) to provide the title N-[(R)-1-(2-benzimidazolyl)thio-2-propyl]-2-chloroadenosine (0.52 g, 51%) mp 213°-215° C. after column chromatography and trituration with dichloromethane; 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 3.95 (1H, q, H-4), 4.12 (1 H, br q, H-3'), 4.42-4.70 (2H, m, --CHCH3 and H-2'), 5.07 (1H, br, 5'-OH), 5.22, 5.50 (2H, 2 br, 2'- and 3'-OH), 5.82 (1H, d, H-1'), 7.04-7.57 (4H, 2m, Ar-H) 8.42 (1H, s, H-2), 8.73 (1H, d, --NH). HPLC retention time 13.7 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Workup

  1. customThe title compound was prepared
  2. customprepared by a Mitsunobu reaction
  3. custompreviously saturated at -10° C.

Sources & evidence

ORD record
ord-eef37df27f68496b8ee408969d3b5262
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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