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

HRID 732908Notes

Reaction equation

HRID 732908 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]([CH3:19])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].I[C:21]1[N:22]=[C:23]([NH2:39])[C:24]2[N:25]=[CH:26][N:27]([C:37]=2[N:38]=1)[C@@H:28]1[O:36][C@H:33]([CH2:34][OH:35])[C@@H:31]([OH:32])[C@H:29]1[OH:30]>>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]([N:7]2[CH2:6][CH2:5][CH:4]([CH2:1][C:2]#[C:3][C:21]3[N:22]=[C:23]([NH2:39])[C:24]4[N:25]=[CH:26][N:27]([C:37]=4[N:38]=3)[C@@H:28]3[O:36][C@H:33]([CH2:34][OH:35])[C@@H:31]([OH:32])[C@H:29]3[OH:30])[CH2:9][CH2:8]2)=[O:11])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 1696622-IodoadenosineHCID 578389144-Methylphenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 250941452-{3-[1-((4-Methyl)phenoxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Procedure

Batch: AB-10-019. 4-methylphenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-105 (0.548 g, 2.130 mmol) was added to a solution of 2-iodoadenosine (0.629 g, 1.600 mmol) according to general procedure 2. Yield: 0.236 g, 28%. 1H NMR (CD3OD) δ 8.29 (s, 1H), 7.14-6.92 (2×m, 4H), 5.95 (d, 1H), 4.75 (m, 2H), 4.34-4.16 (2×m, 3H), 3.91-3.71 (2×d, 2H), 3.10-2.90 (2×bt, 4H), 2.28 (s, 3H), 2.43 (d, 5H), 1.92-1.41 (2×m, 5H). m/Z MH+=523.16. HPLC rt=6.8 min.

Workup

  1. customHPLC rt=6.8 min.

Sources & evidence

ORD record
ord-2bab6b391895411fa54edbdbcfd25609
Source dataset
uspto-grants-2009_09
Patent number
US07589076B2

Reaction notes

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