2-Iodoadenosine → HCID 25093852, compound

HRID 1363981Notes

Reaction equation

HRID 1363981 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][C:14]=2[Cl:19])=[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]>>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][C:10]([N:7]1[CH2:8][CH2:9][CH:4]([CH2:1][C:2]#[C:3][C:21]2[N:22]=[C:23]([NH2:39])[C:24]3[N:25]=[CH:26][N:27]([C:37]=3[N:38]=2)[C@@H:28]2[O:36][C@H:33]([CH2:34][OH:35])[C@@H:31]([OH:32])[C@H:29]2[OH:30])[CH2:5][CH2:6]1)=[O:11]

Participants

3

Reactant 2

HCID 1696622-IodoadenosineHCID 578388912-Chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 25093852HCID 25093852, compound

Procedure

2-Chlorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate (0.588 g, 2.117 mmol) was added to a solution of 2-iodoadenosine (0.602 g, 1.531 mmol) according to general procedure 2: yield 733 mg, 88%. 1H NMR (CD3OD) δ 8.30 (s, 1H), 7.45-7.40, 7.33-7.26, 7.22-7.16 (3×m, 4H), 5.95 (d, 1H, J=6.3 Hz), 4.74 (t, 1H), 4.41-4.30 (m, 2H), 4.20-4.11 (m, 2H), 3.94-3.86, 3.78-3.71, (2×m, 2H), 3.08, 2.92 (2×br t, 2H), 2.43 (d, 2H, J=6.2 Hz), 2.01-1.78, 1.54-1.28 (2×m, 5H). 13C NMR (CD3OD) δ 157.2, 154.3, 150.1, 148.9, 147.4, 142.6, 131.1, 129.0, 128.3, 127.9, 125.4, 120.4, 91.3, 88.2, 86.7, 82.2, 75.5, 72.6, 64.7, 63.5, 45.8, 36.4, 32.4, 26.5, 25.2. LRMS ESI (M+H+) 543.1. HPLC rt=6.2 min.

Workup

  1. customHPLC rt=6.2 min.

Sources & evidence

ORD record
ord-30e39811b6694623a0574644a1cab14a
Source dataset
uspto-grants-2011_02
Patent number
US07888329B2

Reaction notes

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