Methanol → 2-{[4-(Dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid

HRID 13458

Reaction equation

HRID 13458 reaction equation
C(OC(C1C=C([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH3:22])=[C:17]([NH2:23])[CH:16]=2)C=CN=1)=O)(C)(C)C.N[C:25]([NH2:27])=S.Cl.C(N=C=N[CH2:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])C.[N:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([O-:48])=[O:47].F[C:50](F)(F)[C:51](O)=O.[CH3:56]O>C(Cl)Cl.O1CCCC1>[CH3:39][N:37]([CH3:38])[C:36]1[CH:35]=[CH:34][C:51]([NH:27][C:25]2[N:21]([CH3:22])[C:18]3[CH:19]=[CH:20][C:15]([O:14][C:41]4([C:46]([OH:48])=[O:47])[CH:42]=[CH:43][CH:44]=[CH:45][NH:40]4)=[CH:16][C:17]=3[N:23]=2)=[CH:50][CH:56]=1

Participants

9

Reactant 6

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 2723790ThioureaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6920223PicolinateHCID 22040526Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate

Product 1

HCID 866171662-{[4-(Dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 4-(dimethylamino)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. The mixture was then concentrated and to it was added tetrahydrofuran and 1-ethyl-(3-dimethylaminopropyl)carbodimidehydrochloride (2 eq) and stir at ambient temperature for 16 h. tert-butyl4-(2-{[4-dimethylamino)phenyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate crashes out of the reaction mixture. To it in methylene chloride was added trifluoroacetic acid and stirred at ambient temperature overnight. Resulting 4-(2-{[4-dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=403.

Workup

  1. concentrationThe mixture was then concentrated and to it
  2. stirringstirred at ambient temperature overnight
  3. customResulting 4-(2-{[4-dimethylamino)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography

Sources & evidence

ORD record
ord-d628560064ed4f8b9b216bd5fa493048
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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