Pyridine → HCID 86661394, compound

HRID 1256603Notes

Reaction equation

HRID 1256603 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[C:14]([C:16]1[CH:24]=[N:23][CH:22]=[CH:21][C:17]=1[C:18](O)=O)#[CH:15].CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[C:14]([C:16]1[CH:24]=[N:23][CH:22]=[CH:21][C:17]=1[C:18]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]2[N:9]=1)#[CH:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 866613951254166-43-2

Product 1

HCID 86661394HCID 86661394, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.29 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.27 g of 3-ethynylisonicotinic acid, 0.35 g of WSC and 8 ml of pyridine was stirred for 2 hours at 120° C. The reaction mixture was cooled down to room temperature. Into the reaction mixture was poured water, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.15 g of 2-(3-ethynylpyridin-4-yl-)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, referred to as present active compound 211).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2440d83648a4b2084c6490651db33e4
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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