Methyl iodide → 4-[1-Methyl-2-(3-phenoxy-phenylamino)-1h-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid methylamide

HRID 1790719Notes

Reaction equation

HRID 1790719 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([N:14]=[C:15]=S)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:19]1[CH:35]=[C:34]([NH:36][CH3:37])[C:33]([N+:38]([O-])=O)=[CH:32][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]([NH:30][CH3:31])=[O:29])[CH:23]=1.CI>CO>[CH3:31][NH:30][C:28]([C:24]1[CH:23]=[C:22]([O:21][C:20]2[CH:19]=[CH:35][C:34]3[N:36]([CH3:37])[C:15]([NH:14][C:10]4[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:9]=4)=[N:38][C:33]=3[CH:32]=2)[CH:27]=[CH:26][N:25]=1)=[O:29]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 220412813-PhenoxyphenylisothiocyanateHCID 131725843{4-[2-Methoxy-4-(methylamino)-5-nitrophenoxy] (2-pyridyl)}-n-methylcarboxamide

Product 1

HCID 210373624-[1-Methyl-2-(3-phenoxy-phenylamino)-1h-benzoimidazol-5-yloxy]-pyridine-2-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 dram vial was charged with a solution of 3-phenoxyphenylisothiocyanate (23 mg, 0.1 mmol), diamine 1 (27 mg, 0.1 mmol), and MeOH (0.5 mL) and the reaction was shaken at rt overnight. Methyl iodide (8 uL, 0.13 mmol) was added and the mixture shaken overnight. The reaction was concentrated and the resulting residue purified on reverse phase HPLC. LCMS m/z 466.3 (MH+), tR=2.40 min.

Workup

  1. stirringthe mixture shaken overnight
  2. concentrationThe reaction was concentrated
  3. customthe resulting residue purified on reverse phase HPLC

Sources & evidence

ORD record
ord-9dd8ff5a8b8b41219f159bbebd81ad04
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Reaction notes

Loading…