2-Iodoadenosine → HCID 25094144, compound

HRID 732905Notes

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]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].I[C:24]1[N:25]=[C:26]([NH2:42])[C:27]2[N:28]=[CH:29][N:30]([C:40]=2[N:41]=1)[C@@H:31]1[O:39][C@H:36]([CH2:37][OH:38])[C@@H:34]([OH:35])[C@H:32]1[OH:33]>>[CH3:22][O:21][C: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:24]3[N:25]=[C:26]([NH2:42])[C:27]4[N:28]=[CH:29][N:30]([C:40]=4[N:41]=3)[C@@H:31]3[O:39][C@H:36]([CH2:37][OH:38])[C@@H:34]([OH:35])[C@H:32]3[OH:33])[CH2:5][CH2:6]2)=[O:11])=[CH:18][CH:17]=1)=[O:20]

Participants

Reactant 2

HCID 1696622-Iodoadenosine

HCID 57838898HCID 57838898, compound

Product 1

HCID 25094144HCID 25094144, compound

Procedure

Batch: AB-9-151. 4-(methoxycarbonyl)phenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-85 (0.670 g, 2.223 mmol) was added to a solution of 2-iodoadenosine (0.675 g, 1.717 mmol) according to general procedure 2. Yield: 0.648 g, 67%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 8.04-7.20 (2×m, 4H), 5.94 (d, 1H), 4.69 (m, 2H), 4.32-3.71 (4×m, 8H), 3.91-2.71 (2×d, 2H), 3.16-2.90 (2×bt, 4H), 2.48 (d, 5H), 1.98-1.45 (2×m, 5H). m/z MH+=567.14. HPLC rt=7.9 min.

Workup

customHPLC rt=7.9 min.

Sources & evidence

ORD record: ord-abf79ee89f864f298a8c8857a4030232
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589076B2

Reaction notes

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