Pyridine → HCID 72203603, compound

HRID 2272896Notes

Reaction equation

HRID 2272896 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.[CH2:14]([S:16][C:17]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[S:19][C:18]=1[C:26](O)=O)[CH3:15].CCN=C=NCCCN(C)C.Cl.N1C=CC=CC=1>C1C=CC2N(O)N=NC=2C=1.O>[CH2:14]([S:16][C:17]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[S:19][C:18]=1[C:26]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)[CH3:15]

Participants

7

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 117974284HCID 117974284, compound

Product 1

HCID 72203603HCID 72203603, compoundYield 116.2%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.12 g of N2-methyl-5-trifluoromethylpyridine-2,3-diamine, 0.2 g of 3-ethylthio-5-trifluoromethylthiophene-2-carboxylic acid, 0.15 g of EDCI hydrochloride, 9 mg of HOBt and 3 ml of pyridine was stirred at 80° C. for 6 hours. Water was poured into the cooled reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and applied to a silica gel column chromatography to obtain 0.3 g of 2-(3-ethylthio-5-trifluoromethylthiophen-2-yl)-3-methyl-6-t rifluoromethyl-3H-imidazo[4,5,b]pyridine (Compound of Present Invention (5)).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0847a3f44234fee88908b9960fac3db
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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