3-(Benzyloxy)pyridin-2-ol → 1-(6-Azidohexyl)-3-benzyloxypyridine-2-one

HRID 539538Notes

Reaction equation

HRID 539538 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][CH2:33]N1C=CC=C(OC)C1=O)=[N+]=[N-]>>[N:26]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:32][CH2:33][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 711398441-(6-Azidohexyl)-3-benzyloxypyridine-2-oneYield 60%

Procedure

Reaction of 3-benzyloxypyridine-2-one (0.50 g, 2.49 mmol) and 156d (0.66 g, 2.98 mmol) within 16 h as described for synthesis of 157a gave compound 157e (0.48 g, 60%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.15 (m, 5H), 6.65 (dd, J=7.4, 1.8 Hz, 1H), 6.45 (dd, J=7.4, 1.8 Hz, 1H), 5.81 (t, J=7.1 Hz, 1H), 4.92 (s, 2H), 3.76 (t, J=6.8 Hz, 2H), 3.05 (t, J=6.8 Hz, 2H), 1.58 (m, 2H), 1.40 (m, 2H), 1.90 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 157.55, 148.25, 135.95, 128.60, 128.10, 126.95, 126.50, 115.05, 104.90, 70.50, 51.05, 49.20, 28.65, 28.50, 26.20, 25.80. HRMS (FAB) calcd for C18H23N4O2 [M+H]+ 327.1821. found 327.1848.

Sources & evidence

ORD record
ord-f7bca1224ffe44c781a0be14cca0eb03
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

Loading…