2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetic acid → HCID 178521248, compound

HRID 1519841Notes

Reaction equation

HRID 1519841 reaction equation
[Cl: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.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25](O)=[O:26])[C:19](=[O:28])[CH:18]=[CH:17]2>>[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]([NH:7][C:4]1[S:5][CH:6]=[C:2]([Cl:1])[C:3]=1[C:8]1[N:12]=[CH:11][NH:10][N:9]=1)=[O:26])[C:19](=[O:28])[CH:18]=[CH:17]2

Participants

3

Reactant 2

HCID 687845102-(6-bromo-2-oxoquinolin-1(2H)-yl)acetic acidHCID 178509326HCID 178509326, compound

Product 1

HCID 178521248HCID 178521248, compound

Procedure

The title compound was prepared from 4-chloro-3-(1H-1,2,4-triazol-3-yl)thiophen-2-amine (115 mg, 573 umol) and 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetic acid (135 mg, 479 umol) according to protocol A. HPLC purification gave 2-(6-bromo-2-oxoquinolin-1(2H)-yl)-N-(4-chloro-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)acetamide. Method [7] Retention time 5.30 min by HPLC (M+=464, 466, and 468) are the major peak intensities. 1H NMR (300 MHz, CDCl3) δ 7.80 (m, 2H), 7.70 (s, 1H), 7.64 (dd, J=9.0 and 2.4 Hz, 1H), 7.19 (d, J=9.0 Hz, 1H), 6.94 (d, J=9.3 Hz, 1H), 6.82 (s, 1H), 5.30 (s, 2H).

Workup

  1. customHPLC purification

Sources & evidence

ORD record
ord-2a440d2ac7f04fb5b9381c5b66401765
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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