Pyridine → HCID 117988496, compound

HRID 2201347Notes

Reaction equation

HRID 2201347 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.[Cl:14][C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=O.CCN=C=NCCCN(C)C.Cl.N1C=CC=CC=1>O>[Cl:14][C:15]1[C:16]([C:17]2[N:2]([CH3:1])[C:3]3=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]3[N:9]=2)=[CH:20][CH:21]=[CH:22][N:23]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 762582-Chloronicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Product 1

HCID 117988496HCID 117988496, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.96 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.95 g of 2-chloronicotinic acid, 0.85 g of EDCI hydrochloride and 10 ml of pyridine was heated and stirred at 120° C. for 3 hours. Water was poured to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.02 g of 2-(2-chloropyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine. 2-(2-Chloropyridin-3-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

Workup

  1. temperaturewas heated
  2. temperaturecooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7adb061b46744692bcdeae012f7aab10
Source dataset
uspto-grants-2016_06
Patent number
US09364000B2

Reaction notes

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