Methyl iodide → 2-{[3-(Tert-butyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid

HRID 13469Notes

Reaction equation

HRID 13469 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[C:12](OC2C=CC(NC)=C(N)C=2)[CH:11]=[CH:10][N:9]=1)=[O:7])(C)(C)C.NC(N)=S.IC.C(OC(C1C=C([O:43][C:44]2[CH:64]=[CH:63][C:47]3[N:48]([CH3:62])[C:49]([NH:51][C:52]4[CH:57]=[CH:56][CH:55]=[C:54]([C:58]([CH3:61])([CH3:60])[CH3:59])[CH:53]=4)=[N:50][C:46]=3[CH:45]=2)C=CN=1)=O)(C)(C)C.FC(F)(F)C(O)=O>CO.C(Cl)Cl>[C:58]([C:54]1[CH:53]=[C:52]([NH:51][C:49]2[N:48]([CH3:62])[C:47]3[CH:63]=[CH:64][C:44]([O:43][C:8]4([C:6]([OH:7])=[O:5])[CH:13]=[CH:12][CH:11]=[CH:10][NH:9]4)=[CH:45][C:46]=3[N:50]=2)[CH:57]=[CH:56][CH:55]=1)([CH3:60])([CH3:59])[CH3:61]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 2723790ThioureaHCID 22040526Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylateHCID 86592207Tert-butyl-4-(2-{[3-(tert-butyl)phenyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate

Product 1

HCID 865922052-{[3-(Tert-butyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 3-(tert-butyl)benzeneisothiocyanate (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-butyl4-(2-{[3-(tert-butyl)phenyl]amino)-1-methylbenzimidazol-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-(2-{[3-(tert-butyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=416.

Workup

  1. stirringstirred at ambient temperature overnight

Sources & evidence

ORD record
ord-f42f8f662cae4da7b7baf818f6381bee
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

Loading…