3-(Benzyloxy)pyridin-2-ol → 1-(5-Azidopentyl)-3-benzyloxypyridine-2-one

HRID 539537Notes

Reaction equation

HRID 539537 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(OC[CH:22]([N:26]=[N+:27]=[N-:28])[CH2:23][CH2:24][CH3:25])(=O)=O.N([CH2:32]CN1C=CC=C(OC)C1=O)=[N+]=[N-]>>[N:26]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:32][N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]1=[O:15])=[N+:27]=[N-:28]

Participants

4

Reactant 3

HCID 156664523-(Benzyloxy)pyridin-2-olHCID 866750852-Azidopentyl methanesulfonateHCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-one

Product 1

HCID 711397661-(5-Azidopentyl)-3-benzyloxypyridine-2-oneYield 63%

Procedure

Reaction of 3-benzyloxypyridine-2-one (0.50 g, 2.49 mmol) and 156d (0.62 g, 2.98 mmol) within 16 h as described for synthesis of 157a gave compound 157d (0.49 g, 63%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=8.0 Hz, 2H), 7.23 (m, 3H), 6.81 (m, 1H), 6.56 (m, 1H), 5.94 (m, 1H), 5.01 (s, 2H), 3.85 (m, 2H), 3.18 (m, 2H), 1.71 (m, 2H), 1.54 (m, 2H), 1.32 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.68, 148.47, 135.98, 128.60, 128.12, 127.53, 126.93, 115.09, 104.32, 70.27, 50.77, 49.21, 28.19, 28.06, 23.37. HRMS (EI) calcd for C17H20N4O2 [M]+ 312.1586. found 312.1589.

Sources & evidence

ORD record
ord-a2ba1398b17449c893dbd8462a8639eb
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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