Bis-(1H-imidazol-2-YL)-methanone → N-Methyl-3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzamide

HRID 735453Notes

Reaction equation

HRID 735453 reaction equation
[F:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[C:3]=1[CH2:4][N:5]1[C:13]([C:14]2[CH:15]=[C:16]([C:20]#[C:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=O)[CH:17]=[CH:18][CH:19]=2)=[C:12]2[C:7]([C:8]([C:31]([F:34])([F:33])[F:32])=[CH:9][CH:10]=[CH:11]2)=[N:6]1.Cl.CN.C(C1NC=CN=1)([C:46]1[NH:47]C=CN=1)=O>CN(C=O)C>[CH3:46][NH:47][C:25](=[O:27])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([C:21]#[C:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]3[N:5]([CH2:4][C:3]4[C:2]([F:1])=[CH:38][C:37]([F:39])=[CH:36][C:35]=4[F:40])[N:6]=[C:7]4[C:12]=3[CH:11]=[CH:10][CH:9]=[C:8]4[C:31]([F:32])([F:33])[F:34])[CH:15]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 6364545Methylamine hydrochlorideHCID 866030173-({3-[2-(2,4,6-Trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoic acid

Product 1

HCID 86603018N-Methyl-3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzamideYield 39.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenyl}ethynyl)benzoic acid (0.042 g, 0.076 mmol), methyl amine-HCl (0.006 g, 0.076 mmol) and carbonyl diimidazole (0.013 g, 0.076 mmol) in 2 mL DMF was stirred at ambient temperature overnight. The reaction mixture was partitioned with ethyl acetate and H2O. The organic phase was concentrated in vacuo and purified by flash chromatography (silica 60, CH2Cl2—CH3OH, 25:1) to give 0.017 g of the product.

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and H2O
  2. concentrationThe organic phase was concentrated in vacuo
  3. custompurified by flash chromatography (silica 60, CH2Cl2—CH3OH, 25:1)

Sources & evidence

ORD record
ord-65bada7634b6485aac8a1c2da9ae49da
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

Loading…