Ammonia → 2-chloro-N[(R)-1-(1-methyl-2-imidazolyl)thio-2-propyl]adenosine

HRID 375146Notes

Reaction equation

HRID 375146 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[S:8][CH2:9][C@H:10]([NH2:12])[CH3:11].SC1N(C)C=CN=1.C([O:23][C@@H:24]1[C@H:28]([O:29]C(=O)C)[C@@H:27]([CH2:33][O:34]C(=O)C)[O:26][C@H:25]1[N:38]1[CH:46]=[N:45][C:44]2[C:39]1=[N:40][C:41]([Cl:48])=[N:42][C:43]=2Cl)(=O)C.N>>[Cl:48][C:41]1[N:42]=[C:43]([NH:12][C@H:10]([CH3:11])[CH2:9][S:8][C:4]2[N:3]([CH3:2])[CH:7]=[CH:6][N:5]=2)[C:44]2[N:45]=[CH:46][N:38]([C:39]=2[N:40]=1)[C@@H:25]1[O:26][C@H:27]([CH2:33][OH:34])[C@@H:28]([OH:29])[C@H:24]1[OH:23]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 67722751(R)-1-(1-methyl-2-imidazolyl)thio-2-propylamine hydrochlorideHCID 178480602HCID 178480602, compound

Product 1

HCID 228582752-chloro-N[(R)-1-(1-methyl-2-imidazolyl)thio-2-propyl]adenosine

Procedure

The title compound was prepared according to method A as described above in Example 1 by reacting (R)-1-(1-methyl-2-imidazolyl)thio-2-propylamine hydrochloride [prepared using the same method as described in Example 1 from 2-mercapto-1-methylimidazole (3.31 g, 29 mmol) and 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (5.08 g, 29 mmol) followed by acidic hydrolysis] (2.30 g, 11.1 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.46 g, 5.5 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N[(R)-1-(1-methyl-2-imidazolyl)-thio-2-propyl]adenosine (1.1 g, 43%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ 1.28 (3H, d, --CHCH3), 3.53-3.60 (1 H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.95 (1H, q, H- 4'), 4.13 (1H, q, H-3'), 4.51 (1 H, q, H-2'), 5.07 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.82 (1H, d, H-1'), 6.92 (1H, s, Ar-H) 7.20 (1H, s, Ar-H), 8.40 (1H, s, H-8), 8.55 (1H, s, N--H). HPLC retention time 19.3 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Workup

  1. customprepared

Sources & evidence

ORD record
ord-bfd08ca68805460d8382b0de964b6be9
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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