4-Aminophenol → 4-(4-aminophenoxy)-N,N-dimethylpyridine-2-carboxamide

HRID 598499Notes

Reaction equation

HRID 598499 reaction equation
ClC1C=CN=C(C(Cl)=O)C=1.CNC.Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[CH:16]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1>>[CH3:24][N:23]([CH3:25])[C:21]([C:17]1[CH:16]=[C:15]([O:33][C:30]2[CH:31]=[CH:32][C:27]([NH2:26])=[CH:28][CH:29]=2)[CH:20]=[CH:19][N:18]=1)=[O:22]

Participants

5

Reactant 4

HCID 4034-AminophenolHCID 674DimethylamineHCID 49622524-chloro-N,N-dimethylpyridine-2-carboxamideHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 236145634-(4-aminophenoxy)-N,N-dimethylpyridine-2-carboxamide

Procedure

Entry 91: 4-Chloropyridine-2-carbonyl chloride was reacted with dimethylamine according to Method A2, Step 3b. The resulting 4-chloro-N,N-dimethyl-2-pyridinecarboxamide was reacted with 4-aminophenol according to Method A2, Step 4 to give 4-(2-(N,N-dimethylcarbamoyl)-4-pyridyloxy)aniline. 4-Bromo-3-(trifluoromethyl)aniline was converted into 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1. According to Method C1a, 4-bromo-3-(trifluoromethyl)phenyl isocyanate was reacted with 4-(2-(N,N-dimethylcarbamoyl)-4-pyridyloxy)aniline to afford the urea.

Sources & evidence

ORD record
ord-628c002f3af74fd3bd175c0f3313e962
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Reaction notes

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