2-Iodoadenosine → HCID 25093815, compound

HRID 1363978Notes

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]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].I[C:22]1[N:23]=[C:24]([NH2:40])[C:25]2[N:26]=[CH:27][N:28]([C:38]=2[N:39]=1)[C@@H:29]1[O:37][C@H:34]([CH2:35][OH:36])[C@@H:32]([OH:33])[C@H:30]1[OH:31]>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([CH2:1][C:2]#[C:3][C:22]3[N:23]=[C:24]([NH2:40])[C:25]4[N:26]=[CH:27][N:28]([C:38]=4[N:39]=3)[C@@H:29]3[O:37][C@H:34]([CH2:35][OH:36])[C@@H:32]([OH:33])[C@H:30]3[OH:31])[CH2:5][CH2:6]2)=[O:11])=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 1696622-Iodoadenosine

HCID 57838934HCID 57838934, compound

Product 1

HCID 25093815HCID 25093815, compound

Procedure

Batch: AB-10-017. 4-methoxyphenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-103 (597 g, 2.184 mmol) was added to a solution of 2-iodoadenosine (0.649 g, 1.651 mmol) according to general procedure 2. Yield: 0.294 g, 33%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 7.00-6.87 (2×m, 4H), 5.94 (d, 1H), 4.73 (m, 2H), 4.33-4.14 (2×m, 3H), 3.92-3.76 (2×d, 5H), 3.10-2.90 (2×bt, 4H), 2.46 (d, 5H), 1.91-1.40 (2×m, 5H). m/z MH+=539.14. HPLC rt=5.5 min.

Workup

customHPLC rt=5.5 min.

Sources & evidence

ORD record: ord-b9f9824a8b714f8aafa2b16bdb0f8aa4
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888329B2

Reaction notes

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