Ammonia → HCID 53884295, compound

HRID 1082100Notes

Reaction equation

HRID 1082100 reaction equation
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:24][C:25]#[N:26])[O:12][C@H:11]1[N:27]1[C:49]2[N:48]=[C:47]([Cl:50])[N:46]=[C:31]([NH:32][N:33]3[CH2:38][CH2:37][CH:36]([S:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:35][CH2:34]3)[C:30]=2[N:29]=[CH:28]1)(=O)C1C=CC=CC=1.N.C(OCC)(=O)C>CO>[Cl:50][C:47]1[N:46]=[C:31]([NH:32][N:33]2[CH2:34][CH2:35][CH:36]([S:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:37][CH2:38]2)[C:30]2[N:29]=[CH:28][N:27]([C:49]=2[N:48]=1)[C@@H:11]1[O:12][C@H:13]([CH2:24][C:25]#[N:26])[C@@H:14]([OH:15])[C@H:10]1[OH:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 22868436HCID 22868436, compound

Product 1

HCID 53884295HCID 53884295, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared by general method A, described in more detail in Example 22. 2',3'-Di-O-benzoyl-2-chloro-5'-cyano-5'-deoxy-N-(4-phenylthio-1-piperidinyl)adenosine [prepared from 1-amino-6-phenylthiopiperidine (Knutsen, L. J. S., Lau, J., Sheardown, M. J., Thomsen, C.; Bioorganic and Medicinal Chemistry Letters, 1993, 3, 2661-2666) and 9-(2',3'-di-O-benzoyl-5'-cyano-5'-deoxy-β-D-ribofuranosyl)-2,6-dichloro-9H-purine as described in Example 24] (1.5 g, 2.5 mmol) in methanol (20 ml) was treated with methanolic ammonia (5 ml). The reaction mixture was stirred at ambient temperature for 0.75 h. Ethyl acetate (5 ml) was added to the residue on evaporation to provide 2-chloro-5'-cyano-5'-deoxy-N-(4-phenylthio-1-piperidinyl)adenosine (0.11 g, 46%) as a solid, m.p. 159°-161° C., 1H-NMR (400 MHz, DMSO-d6) δ1.68 (2H, br q, piperidine C--H), 1.98 (2H, m, piperidine C--H), 2.78 (2H, br, piperidine C--H), 3.04 (2H, br d, H-5'a and H-5'b), 4.11 (2H, m, H-4' and H-3'), 4.63 (1H, m, H-2'), 5.54, 5.68 (2H, 2d, 2'-and 3'-OH), 5.88 (1H, d, H-1'), 7.22-7.45 (5H, 3m, Ar--H), 8.38 (1H, s, H-8), 9.49 (1H, s, N--H). HPLC retention time 20.34 min. (gradient elution over 30 min; 25-45% acetonitrile/0.1% ammonium sulfate in water), purity 96% at 250 nm). C16H20ClN7O3. 0.7 H2O. 0.1 EtOAc requires C, 51.4; H, 5.1; N, 18.7. Found C, 51.4; H, 4.9; N, 18.3%.

Workup

  1. customThis compound was prepared by general method A

Sources & evidence

ORD record
ord-b089c6e611f94b0f9d73a326728acc84
Source dataset
uspto-grants-1996_12
Patent number
US05589467

Reaction notes

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