Ammonia → HCID 44323684, compound

HRID 1901531Notes

Reaction equation

[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([OH:8])[CH2:3]1.C([O:17][C@@H:18]1[C@H:22]([O:23]C(=O)C2C=CC=CC=2)[C@@H:21]([CH2:32][O:33]C(=O)C2C=CC=CC=2)[O:20][C@H:19]1[N:42]1[CH:50]=[N:49][C:48]2[C:43]1=[N:44][C:45]([Cl:52])=[N:46][C:47]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:52][C:45]1[N:46]=[C:47]([NH:1][N:2]2[CH2:7][CH2:6][CH2:5][CH:4]([OH:8])[CH2:3]2)[C:48]2[N:49]=[CH:50][N:42]([C:43]=2[N:44]=1)[C@@H:19]1[O:20][C@H:21]([CH2:32][OH:33])[C@@H:22]([OH:23])[C@H:18]1[OH:17]

Participants

Reactant 3

HCID 222Ammonia

HCID 2586913-Piperidinol, 1-amino-

HCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purine

Product 1

HCID 44323684HCID 44323684, compoundYield 8%

Procedure

The title compound was prepared according to method A as described above by reacting 1-amino-3-hydroxypiperidine (prepared from 3-hydroxypiperidine as outlined in Example 6) (0.60 g, 5.9 mmol) with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.50 g, 3.94 mmol), followed by debenzoylation of the purified product using methanolic ammonia to provide the title 2-chloro-N-(3-hydroxypiperidinyl) adenosine (0.12 g, 8%) (after column chromatography) as a foam (a mixture of diastereoisomers); 1H NMR (DMSO-d6) δ 3.52-3.60 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.14 (1H, m, H-3'), 4.52 (1H, m, H-2'), 5.08 (1H, t, 5'-0H), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 8.43 (1H, br s, H-8), 9.45 (1H, 2 br s, N--H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-51ee6cc2a3204dc99ff26ce5349ea6d2
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578582

Reaction notes

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