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

HRID 1514061Notes

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]([F: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]>>[F: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: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])[CH2:5][CH2:6]2)=[O:11])=[CH:18][CH:17]=1

Participants

Reactant 2

HCID 1696622-Iodoadenosine

HCID 578389024-Fluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 250941432-{3-[1-((4-Fluorophenoxy)carbonyl)piperidin-4-yl]propyn-1-yl}adenosine

Procedure

Batch: AB-9-147. 4-fluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate, batch JR28-97 (0.700 g, 2.68 mmol) was added to a solution of 2-iodoadenosine (0.812 g, 2.065 mmol) according to general procedure 2. Yield: 0.902 g, 83%. 1H NMR (CD3OD) δ 8.34 (s, 1H), 7.11 (m, 4H), 5.98 (d, 1H), 4.76 (m, 2H), 4.37-4.19 (2×m, 3H), 3.95-3.75 (2×d, 2H), 3.07-2.93 (2×bt, 4H), 2.47 (d, 5H), 1.98-1.44 (2×m, 5H). m/z MH+=527.19. HPLC rt=7.6 min.

Workup

customHPLC rt=7.6 min.

Sources & evidence

ORD record: ord-e3cfe6b70f49445c9d5d5f58ebedaf21
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222228B2

Reaction notes

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