2-(6-cyano-2-oxoquinolin-1(2H)-yl)acetic acid → HCID 178509474, compound

HRID 2098056Notes

Reaction equation

HRID 2098056 reaction equation
[Br:1][C:2]1[C:3]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([NH2:7])[S:5][CH:6]=1.[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:25][C:26](O)=[O:27])[C:20](=[O:29])[CH:19]=[CH:18]2)#[N:14]>>[Br:1][C:2]1[C:3]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[C:4]([NH:7][C:26](=[O:27])[CH2:25][N:21]2[C:22]3[C:17](=[CH:16][C:15]([C:13]#[N:14])=[CH:24][CH:23]=3)[CH:18]=[CH:19][C:20]2=[O:29])[S:5][CH:6]=1

Participants

3

Reactant 2

HCID 687860092-(6-cyano-2-oxoquinolin-1(2H)-yl)acetic acidHCID 178509324HCID 178509324, compound

Product 1

HCID 178509474HCID 178509474, compound

Procedure

The title compound was prepared from 4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-amine (253 mg, 1.03 mmol) and 2-(6-cyano-2-oxoquinolin-1(2H)-yl)acetic acid (325 mg, 1.42 mmol) according to protocol A. HPLC purification gave N-(4-bromo-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(6-cyano-2-oxoquinolin-1(2H)-yl)acetamide. Method [7] Retention time 4.00 min by HPLC (M+=455 and 457). 1H NMR (300 MHz, DMSO-d6) δ 8.42 (broad s, 1H), 8.37 (s, 1H), 8.13 (d, J=9.9 Hz, 1H), 7.98 (d, J=9.0 Hz, 1H), 7.70 (d, J=9.0 Hz, 1H), 7.27 (s, 1H), 6.87 (d, J=9.3 Hz, 1H), 5.30 (s, 2H).

Workup

  1. customHPLC purification

Sources & evidence

ORD record
ord-d44651b5f31744ebb03f88a066bb7cc2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

Loading…