Methyl iodide → 4-{1-Methyl-2-[(4-methylphenyl)amino]benzimidazol-5-yloxy)pyridine-2-carboxylic acid

HRID 13466Notes

Reaction equation

HRID 13466 reaction equation
C(OC(C1C=C(OC2C=CC(NC)=C(N)C=2)C=CN=1)=O)(C)(C)C.NC(N)=S.IC.C([O:34][C:35]([C:37]1[CH:42]=[C:41]([O:43][C:44]2[CH:61]=[CH:60][C:47]3[N:48]([CH3:59])[C:49]([NH:51][C:52]4[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=4)=[N:50][C:46]=3[CH:45]=2)[CH:40]=[CH:39][N:38]=1)=[O:36])(C)(C)C.FC(F)(F)C(O)=O>CO.C(Cl)Cl>[CH3:59][N:48]1[C:47]2[CH:60]=[CH:61][C:44]([O:43][C:41]3[CH:40]=[CH:39][N:38]=[C:37]([C:35]([OH:36])=[O:34])[CH:42]=3)=[CH:45][C:46]=2[N:50]=[C:49]1[NH:51][C:52]1[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 2723790ThioureaHCID 22040526Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylateHCID 86617168Tert-butyl-4-{1-methyl-2-[(4-methylphenyl)amino)benzimidazol-5-yloxy)pyridine-2-carboxylate

Product 1

HCID 220411164-{1-Methyl-2-[(4-methylphenyl)amino]benzimidazol-5-yloxy)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To tert-butyl-4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-methylbenzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. Formation of tert-butyl-4-{1-methyl-2-[(4-methylphenyl)amino)benzimidazol-5-yloxy)pyridine-2-carboxylate was followed by LC/MS. To it in methylene chloride was added trifluoroacetic acid and stirred at ambient temperature overnight. Resulting 4-{1-methyl-2-[(4-methylphenyl)amino]benzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=374.

Workup

  1. stirringstirred at ambient temperature overnight
  2. customResulting 4-{1-methyl-2-[(4-methylphenyl)amino]benzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography

Sources & evidence

ORD record
ord-9605a6eb01924c56bfd789935555b745
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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