6-(2-Azidoethoxy)-2-phenylchroman-4-one → HCID 17978599, compound

HRID 31261Notes

Reaction equation

HRID 31261 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].C1(C2CCC3C(=CC=C(OCCN)C=3)O2)C=CC=CC=1.[N:26]([CH2:29][CH2:30][O:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[O:38][CH:37]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:36][C:35]2=[O:48])=[N+]=[N-]>>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH2:26][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[O:38][CH:37]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:36][C:35]2=[O:48]

Participants

3

Reactant 2

HCID 179785726-(2-Azidoethoxy)-2-phenylchroman-4-oneHCID 17978593HCID 17978593, compound

Product 1

HCID 17978599HCID 17978599, compound

Procedure

6-(2-Aminoethoxy)-2-phenylchroman-4-one methane sulfonate was prepared as described for 2-(2-phenylchroman-6-yloxy)ethylamine methane sulfonate in Example 4 (b) starting from 6-(2-azidoethoxy)-2-phenylchroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 7.91 (bs, 3H), 7.55-7.54 (m, 2H), 7.46-7.37 (m, 3H), 7.31 (d, 1H, J 3.1 Hz), 7.28 (dd, 1H, 8.8, 3.1 Hz), 7.12 (d, 1H, 8.8 Hz), 5.63 (dd, 1H, 13.0, 3.0 Hz), 4.17 (t, 2H, J 5.1 Hz), 3.25 (dd, 1H, J −16.9, 13.0 Hz), 3.23 (m, 2H), 2.86 (dd, 1H, J −16.9, 3.0 Hz), 2.29 (s, 3H).

Sources & evidence

ORD record
ord-7a69d156f3644eea99fab36660cfe2c4
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…