2-Iodoadenosine → 2-{3-[1-((4-Nitrophenoxy)carbonyl)piperidin-4-yl]propyn-1-yl}adenosine

HRID 732904Notes

Reaction equation

HRID 732904 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].I[C:23]1[N:24]=[C:25]([NH2:41])[C:26]2[N:27]=[CH:28][N:29]([C:39]=2[N:40]=1)[C@@H:30]1[O:38][C@H:35]([CH2:36][OH:37])[C@@H:33]([OH:34])[C@H:31]1[OH:32]>>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([CH2:1][C:2]#[C:3][C:23]3[N:24]=[C:25]([NH2:41])[C:26]4[N:27]=[CH:28][N:29]([C:39]=4[N:40]=3)[C@@H:30]3[O:38][C@H:35]([CH2:36][OH:37])[C@@H:33]([OH:34])[C@H:31]3[OH:32])[CH2:5][CH2:6]2)=[O:11])=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 1696622-IodoadenosineHCID 578388894-Nitrophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 250941062-{3-[1-((4-Nitrophenoxy)carbonyl)piperidin-4-yl]propyn-1-yl}adenosine

Procedure

Batch: AB-9-149. 4-nitrophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-97 (0.630 g, 2.185 mmol) was added to a solution of 2-iodoadenosine (0.727 g, 1.849 mmol) according to general procedure 2. Yield: 1.192 g, 65%. %. 1H NMR (CD3OD) δ 8.26 (m, 1H), 8.25-7.34 (2×m, 4H), 5.94 (d, 1H), 4.72 (m, 2H), 4.32-4.14 (2×m, 3H), 3.91-3.71 (2×d, 2H), 3.17-2.90 (2×bt, 4H), 2.48 (d, 5H), 1.45 (m, 5H). m/z MH+=554.15. HPLC rt=7.3 mm.

Workup

  1. customHPLC rt=7.3 mm

Sources & evidence

ORD record
ord-3dbfef74a8454c3194f1bfb421c4be68
Source dataset
uspto-grants-2009_09
Patent number
US07589076B2

Reaction notes

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