Water → [4-(5-Amino-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-(2-fluoro-4-iodo-phenyl)-amine

HRID 658382Notes

Reaction equation

HRID 658382 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[N:18][CH:17]=[CH:16][C:11]=1[C:12]([NH:14][NH2:15])=O.I.CS[CH:23]([NH2:25])[NH2:24].O>N1C=CC=CC=1>[NH2:25][C:23]1[NH:24][C:12]([C:11]2[CH:16]=[CH:17][N:18]=[CH:19][C:10]=2[NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])=[N:14][N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 115888023-[(2-Fluoro-4-iodophenyl)amino]isonicotinohydrazideHCID 86616903C-Methylsulfanyl-methanediamine hydroiodide

Product 1

HCID 178509141[4-(5-Amino-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-(2-fluoro-4-iodo-phenyl)-amineYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

A reaction mixture of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid hydrazide (100 mg, 0.27 mmol, 1 eq) and C-Methylsulfanyl-methanediamine hydroiodide (86 mg, 0.39 mmol, 1.45 eq) in pyridine (2 mL) in a sealed tube was heated at 140° C. for 4 hrs. After cooling the mixture was poured into water, extracted with EtOAc, and the combined organic fractions were dried over anhydrous MgSO4. After filtration and solvent evaporation the resulting residue was subjected to silica gel column chromatography (EtOAC:Hex=1:1) to give the desired product (46 mg). [4.99 min; 397(M+1)]

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with EtOAc
  3. dry with materialthe combined organic fractions were dried over anhydrous MgSO4
  4. filtrationAfter filtration and solvent evaporation the resulting residue

Sources & evidence

ORD record
ord-05c2ab68af3b41a4b192fd1ca41bc206
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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