6-[6-(1-Ethoxy-vinyl)[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinoline → 6-(1-(6-(1-Ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-7-fluoroquinoline

HRID 456143

Reaction equation

HRID 456143 reaction equation
[CH2:1]([O:3][C:4](C1N=C2N(CC3C=C4C(=CC=3)N=CC=C4)N=NC2=NC=1)=[CH2:5])[CH3:2].Br[C:27]1[N:32]=[C:31]2[N:33]([CH:36]([C:38]3[CH:39]=[C:40]4[C:45](=[CH:46][C:47]=3[F:48])[N:44]=[CH:43][CH:42]=[CH:41]4)[CH3:37])[N:34]=[N:35][C:30]2=[N:29][CH:28]=1>>[CH2:4]([O:3][C:1]([C:27]1[N:32]=[C:31]2[N:33]([CH:36]([C:38]3[CH:39]=[C:40]4[C:45](=[CH:46][C:47]=3[F:48])[N:44]=[CH:43][CH:42]=[CH:41]4)[CH3:37])[N:34]=[N:35][C:30]2=[N:29][CH:28]=1)=[CH2:2])[CH3:5]

Participants

3

Reactant 2

HCID 248519576-[6-(1-Ethoxy-vinyl)[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinolineHCID 866660826-(1-(6-Bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-7-fluoroquinoline

Product 1

HCID 669272076-(1-(6-(1-Ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-7-fluoroquinoline

Procedure

The title compound was prepared in analogy to the synthesis of compound 52.3 from 6-(1-(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-7-fluoroquinoline. 1H-NMR (400 MHz, CDCl3) δ ppm 9.17 (9.17 (s, 1H), 8.90 (m, 1H), 8.10 (d, 1H), 7.89 (d, 1H), 7.78 (d, 1H), 7.39 (dd, 1H), 6.82 (q, 1H), 5.56 (d, 1H), 4.56 (d, 1H), 4.04 (q, 2H), 2.30 (d, 3H), 1.48 (t, 3H). LCMS (method B): [MH]+=365, tR=2.55 min.

Sources & evidence

ORD record
ord-d37acd31ff2849e687719bb64c565e21
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

Loading…