4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine → N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(6-ethynyl-2-oxoquinolin-1(2H)-yl)acetamide

HRID 2098102Notes

Reaction equation

HRID 2098102 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]([OH:16])=O)[C:8](=[O:17])[CH:7]=[CH:6]2)#[CH:2].[Br:18][C:19]1[C:20]([C:25]2[NH:29][N:28]=[CH:27][N:26]=2)=[C:21]([NH2:24])[S:22][CH:23]=1>>[Br:18][C:19]1[C:20]([C:25]2[NH:29][N:28]=[CH:27][N:26]=2)=[C:21]([NH:24][C:14](=[O:16])[CH2:13][N:9]2[C:10]3[C:5](=[CH:4][C:3]([C:1]#[CH:2])=[CH:12][CH:11]=3)[CH:6]=[CH:7][C:8]2=[O:17])[S:22][CH:23]=1

Participants

3

Reactant 2

HCID 596366864-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amineHCID 866494242-(6-Ethynyl-2-oxoquinolin-1(2H)-yl)acetic acid

Product 1

HCID 59636680N-(4-Bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-yl)-2-(6-ethynyl-2-oxoquinolin-1(2H)-yl)acetamide

Procedure

The title compound was synthesized from 2-(6-ethynyl-2-oxoquinolin-1(2H)-yl)acetic acid and 4-bromo-3-(1H-1,2,4-triazol-5-yl)thiophen-2-amine according to protocol A. Retention time (min)=6.563, method [7], MS (ESI) 454.0 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.07 (d, J=9.35 Hz, 1H), 8.01-7.97 (m, 1H), 7.68-7.63 (m, 1H), 7.50 (d, J=8.80 Hz, 1H), 7.30 (s, 1H), 6.80 (d, J=9.9 Hz, 1H), 5.27 (s, 2H), 4.23 (s, 1H).

Sources & evidence

ORD record
ord-11d6a6d8060449cbbd41c43e7d3b02ea
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…