4-Chloro-N-methylpicolinamide → 4-(4-Amino-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

HRID 404708Notes

Reaction equation

HRID 404708 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CC(C)([O-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH:25][CH3:26])=[O:24])[CH:18]=1>CN(C)C(=O)C>[CH3:26][NH:25][C:23]([C:19]1[CH:18]=[C:17]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([F:9])[CH:4]=2)[CH:22]=[CH:21][N:20]=1)=[O:24]

Participants

5

Reactant 3

HCID 14768144-Chloro-N-methylpicolinamideHCID 27359194-Amino-3-fluorophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 468352194-(4-Amino-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In the first step 4-amino-3-fluorophenol was treated with potassium tert-butoxide and 4-chloro-N-methyl-2-pyridinecarboxamide was added in N,N-dimethylacetamide to form 4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methylamide which after extraction was finally treated with 4-chloro-3-(trifluoromethyl)phenyl isocyanate in toluene to form 4{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide which is the compound of formula (I).

Sources & evidence

ORD record
ord-ff50c7ba24b9433eb9301ba7970c980b
Source dataset
uspto-grants-2014_06
Patent number
US08748622B2

Reaction notes

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