Ammonia → HCID 9934714, compound

HRID 1647524Notes

Reaction equation

OC1CCNCC1.[NH2:8][N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1.C([O:30][C@@H:31]1[C@H:35]([O:36]C(=O)C2C=CC=CC=2)[C@@H:34]([CH2:45][O:46]C(=O)C2C=CC=CC=2)[O:33][C@H:32]1[N:55]1[CH:63]=[N:62][C:61]2[C:56]1=[N:57][C:58]([Cl:65])=[N:59][C:60]=2Cl)(=O)C1C=CC=CC=1.N>>[Cl:65][C:58]1[N:59]=[C:60]([NH:8][N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)[C:61]2[N:62]=[CH:63][N:55]([C:56]=2[N:57]=1)[C@@H:32]1[O:33][C@H:34]([CH2:45][OH:46])[C@@H:35]([OH:36])[C@H:31]1[OH:30]

Participants

Reactant 4

HCID 222Ammonia

HCID 79341Piperidin-4-ol

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

HCID 233677104-Phenoxy-1-piperidinamine

Product 1

HCID 9934714HCID 9934714, compoundYield 57%

Procedure

This compound was prepared from 4-hydroxypiperidine using the methodology described in Example 16. 1-Amino-4-phenoxypiperidine (0.96 g, 5.0 mmol) was reacted with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.50 g, 4 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-(4-phenoxy-1-piperidinyl)adenosine 1.07 g, 57%) as a foam, 1H NMR (DMSO-d6) δ3.52-3.60 (1H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.95 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.43-4.54 (2H, m, H-2' and --C--H), 5.07 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 6.90-7.33 (5H, 2m, Ar-H), 8.42 (1H, s, H-8), 9.49 (1H, s, N-H).

Sources & evidence

ORD record: ord-94f5552125ee4051b05ddaf7b2663323
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05432164

Reaction notes

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