Water → HCID 178427893, compound

HRID 658376Notes

Reaction equation

HRID 658376 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[N:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][NH2:14])=O)=[C:4]([CH3:19])[CH:3]=1.I.CS[CH:23]([NH2:25])[NH2:24].O>N1C=CC=CC=1>[NH2:25][C:23]1[NH:24][C:11]([C:10]2[CH:15]=[CH:16][N:17]=[CH:18][C:9]=2[NH:8][C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=2[CH3:19])=[N:13][N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 688544153-(4-Iodo-2-methyl-phenylamino)-isonicotinic acid hydrazideHCID 86616903C-Methylsulfanyl-methanediamine hydroiodide

Product 1

HCID 178427893HCID 178427893, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

A reaction mixture of 3-(4-Iodo-2-methyl-phenylamino)-isonicotinic acid hydrazide (120 mg, 0.33 mmol, 1 eq) and C-Methylsulfanyl-methanediamine hydroiodide (104 mg, 0.47 mL, 1.45 eq) in pyridine (2 mL) in sealed tube was heated to 140° C. while stirring for 4 hrs. After cooling, it was poured into water, extracted with EtOAc, and the combined organic fractions, dried over anhydrous MgSO4. After filtration and solvent removal the remaining crude product was subjected to silica gel column chromatography (eluent:Hexane EtOAc=1:1) to afford the desired product (35 mg). [4.26 min; 393(M+1)]

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. dry with materialthe combined organic fractions, dried over anhydrous MgSO4
  4. filtrationAfter filtration and solvent removal the remaining crude product

Sources & evidence

ORD record
ord-dc361f542a62499e816501e59e002d33
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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