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

HRID 1363973Notes

Reaction equation

HRID 1363973 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].I[C:20]1[N:21]=[C:22]([NH2:38])[C:23]2[N:24]=[CH:25][N:26]([C:36]=2[N:37]=1)[C@@H:27]1[O:35][C@H:32]([CH2:33][OH:34])[C@@H:30]([OH:31])[C@H:28]1[OH:29]>>[O:12]([C:10]([N:7]1[CH2:6][CH2:5][CH:4]([CH2:1][C:2]#[C:3][C:20]2[N:21]=[C:22]([NH2:38])[C:23]3[N:24]=[CH:25][N:26]([C:36]=3[N:37]=2)[C@@H:27]2[O:35][C@H:32]([CH2:33][OH:34])[C@@H:30]([OH:31])[C@H:28]2[OH:29])[CH2:9][CH2:8]1)=[O:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 1696622-IodoadenosineHCID 57838938Phenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 250939632-{3-[1-(Phenoxycarbonyl)piperidin-4-yl]propyn-1-yl}adenosine

Procedure

Batch: AB-9-97. Phenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-11 (0.329 g, 1.352 mmol) was added to a solution of 2-iodoadenosine (0.513 g, 1.305 mmol) according to general procedure 2. Yield: 54.5 mg, 82%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 7.38-7.06 (3×m, 5H), 5.94 (d, 1H), 4.71 (m, 1H), 4.32-4.17 (2×m, 7H), 3.92-3.72 (2×d, 2H), 3.10-2.90 (2×bt, 4H), 2.48 (d, 5H), 1.93 (2×m, 5H). m/z MH+=509.18. HPLC rt=5.3 min.

Workup

  1. customHPLC rt=5.3 min.

Sources & evidence

ORD record
ord-e79b0238521b41758b1e65caa0ba214c
Source dataset
uspto-grants-2011_02
Patent number
US07888329B2

Reaction notes

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