2-(3,3-Difluoro-2-oxoindolin-1-yl)acetic acid → N-(4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3,3-difluoro-2-oxoindolin-1-yl)acetamide

HRID 1519848Notes

Reaction equation

HRID 1519848 reaction equation
[F:1][C:2]1([F:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([OH:14])=O)[C:3]1=[O:15].[Br:17][C:18]1[C:19]([C:24]2[NH:28][CH:27]=[N:26][N:25]=2)=[C:20]([NH2:23])[S:21][CH:22]=1>>[Br:17][C:18]1[C:19]([C:24]2[NH:28][CH:27]=[N:26][N:25]=2)=[C:20]([NH:23][C:12](=[O:14])[CH2:11][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([F:1])([F:16])[C:3]2=[O:15])[S:21][CH:22]=1

Participants

3

Reactant 2

HCID 687551942-(3,3-Difluoro-2-oxoindolin-1-yl)acetic acidHCID 178509325HCID 178509325, compound

Product 1

HCID 178521255N-(4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3,3-difluoro-2-oxoindolin-1-yl)acetamideYield 14.7%

Procedure

The title compound was prepared from 2-(3,3-difluoro-2-oxoindolin-1-yl)acetic acid (50 mg, 0.22 mmol), 4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine (45 mg, 0.18 mmol) using protocol A. HPLC purification gave N-(4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(3,3-difluoro-2-oxoindolin-1-yl)acetamide (12 mg) as a white solid (m/z 454.0, retention of 5.696 min in [7]). 1H-NMR (300MHz, CDCl3) δ 13.1 (s, 1H), 7.82 (s, 1H), 7.70 (dd, J=7.5, 1.5Hz, 1H), 7.50 (td, J=7.9, 1.2Hz, 1H), 6.99 (s, 1H), 6.92 (d, J=7.9Hz, 1H), 4.71 (s, 2H).

Workup

  1. customHPLC purification

Sources & evidence

ORD record
ord-21f0eda03c52400ba880c468efead3e0
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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