2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 22858293, compound

HRID 375159Notes

Reaction equation

HRID 375159 reaction equation
Cl.NC1C=CC2N=C(S[C@@H](CC(N)C)CC)SC=2C=1.NC1C=CC2N=C(S)SC=2C=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:63][C@@H:64]1[C@H:68]([O:69]C(=O)C)[C@@H:67]([CH2:73][O:74]C(=O)C)[O:66][C@H:65]1[N:78]1[C:101]2[N:100]=[C:99]([Cl:102])[N:98]=[C:82]([NH:83][C@H:84]([CH3:97])[CH2:85][S:86][C:87]3[S:88][C:89]4[CH:95]=[C:94]([NH2:96])[CH:93]=[CH:92][C:90]=4[N:91]=3)[C:81]=2[N:80]=[CH:79]1)(=O)C>N>[NH2:96][C:94]1[CH:93]=[CH:92][C:90]2[N:91]=[C:87]([S:86][CH2:85][C@H:84]([NH:83][C:82]3[C:81]4[N:80]=[CH:79][N:78]([C:101]=4[N:100]=[C:99]([Cl:102])[N:98]=3)[C@@H:65]3[O:66][C@H:67]([CH2:73][OH:74])[C@@H:68]([OH:69])[C@H:64]3[OH:63])[CH3:97])[S:88][C:89]=2[CH:95]=1

Participants

6

Reactant 4

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 22858314HCID 22858314, compoundHCID 67771529HCID 67771529, compoundHCID 178418618HCID 178418618, compound

Product 1

HCID 22858293HCID 22858293, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The title compound was prepared according to general method A as described above in Example 1 by reacting 6-amino-2-[(R)-2-aminopropyl-1-propylthio]benzothiazole hydrochloride [prepared by a Mitsunobu reaction as described in Example 1 using 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (13.1 g, 75 mmol) and 6-amino-2-mercaptobenzothiazole (13.7 g, 75 mmol) followed by acidic hydrolysis]) (2.51 g, 7.2 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.68 g, 6.0 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(6-amino-2-benzothiazolyl)thio-2-propyl]-2-chloroadenosine in methanolic ammonia (200 ml) (previously saturated at -10° C.) to provide the title N-[(R)-1-(6-amino2-benzothiazolyl)thio-2-propyl]-2chloroadenosine (1.97 g, 63%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.36 (3H, d, --CHCH3), 3,50-3.71 (4H, m, H-5'a and H-5'b and --CH2 --), 3.95 (1H, d, H-4'), 4.14 (1H, d, H-3'), 4.53 (1H, q, H-2'), 4.63 (1H, m, --CH), 5.08 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 6.71, 6.99, 7.53 (3H, 3d, Ar-H), 8.41 (1H, s, H-8), 8.52 (1H, d, N--H). HPLC retention time 10.29 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-8102e45011fa48058bb6a27bd6d36ef7
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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