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

HRID 1363984Notes

Reaction equation

HRID 1363984 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])=[C:15]([F:20])[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]>>[F:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[F:19])[O:12][C:10]([N:7]1[CH2:6][CH2:5][CH:4]([CH2:1][C:2]#[C:3][C:22]2[N:23]=[C:24]([NH2:40])[C:25]3[N:26]=[CH:27][N:28]([C:38]=3[N:39]=2)[C@@H:29]2[O:37][C@H:34]([CH2:35][OH:36])[C@@H:32]([OH:33])[C@H:30]2[OH:31])[CH2:9][CH2:8]1)=[O:11]

Participants

3

Reactant 2

HCID 1696622-IodoadenosineHCID 578388903,4-Difluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 250939192-{3-[1-((3,4-Difluoro)phenoxycarbanoyl)piperidin-4-yl]propyn-1-yl}adenosine

Procedure

3,4-Difluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate (1.830 g, 6.55 mmol) was added to a solution of 2-iodoadenosine (0.611 g, 1.554 mmol) according to general procedure 2: yield 201 mg, 24%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 7.25 (m, 1H), 7.12 (m, 1H), 6.96-6.89 (m, 1H), 5.93 (d, 1H, J=6.5 Hz), 4.71 (dd, 1H, J=5.1 Hz, J=6.4 Hz), 4.35-4.24 (m, 2H), 4.23-4.13 (m, 2H), 3.89 (dd, 1H, J=2.3 Hz, J=12.6 Hz), 3.74 (dd, 1H, J=2.5, J=12.6 Hz), 3.05, 2.91 (2×br t, 2H), 2.46 (d, 2H, J=6.2 Hz), 2.01-1.79, 1.52-1.27 (2×m, 5H). LRMS ESI (M+H+) 545.2. HPLC rt=9.1 min.

Workup

  1. customHPLC rt=9.1 min.

Sources & evidence

ORD record
ord-226d17e56df243e4949bb6e1c14cae25
Source dataset
uspto-grants-2011_02
Patent number
US07888329B2

Reaction notes

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