Methyl iodide → 2-{[4-Chlorophenylamino)-6-methoxy-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid

HRID 13493Notes

Reaction equation

HRID 13493 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[C:12](OC2C(OC)=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:45][C:46]2[CH:63]=[CH:62][C:49]3[N:50]([CH3:61])[C:51]([NH:53][C:54]4[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][CH:55]=4)=[N:52][C:48]=3[CH:47]=2)C=CN=1)=O)(C)(C)C.FC(F)(F)[C:66](O)=[O:67]>CO.C(Cl)Cl>[Cl:60][C:57]1[CH:56]=[CH:55][C:54]([NH:53][C:51]2[N:50]([CH3:61])[C:49]3[CH:62]=[C:63]([O:67][CH3:66])[C:46]([O:45][C:8]4([C:6]([OH:7])=[O:5])[CH:13]=[CH:12][CH:11]=[CH:10][NH:9]4)=[CH:47][C:48]=3[N:52]=2)=[CH:59][CH:58]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 2723790ThioureaHCID 68430819Tert-butyl4-[3-amino-6-methoxy-4-(methylamino)phenoxy]pyridine-2-carboxylateHCID 86592213Tert-butyl4-(2-{[4-chlorophenyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate

Product 1

HCID 865922122-{[4-Chlorophenylamino)-6-methoxy-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To tert-butyl4-[3-amino-6-methoxy-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-chlorobenzeneisothiocyanate (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-{[4-chlorophenyl]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-{[4-chlorophenylamino)-6-methoxy-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=424.

Workup

  1. stirringstirred at ambient temperature overnight

Sources & evidence

ORD record
ord-dd3a13bb614743c5808027ed3e159b73
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Reaction notes

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