4-Aminophenol → 4-(2-(N-ethylcarbamoyl)-4-pyridyloxy)aniline

HRID 78348

Reaction equation

HRID 78348 reaction equation
ClC1C=CN=C(C(Cl)=O)C=1.C(N)C.Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])[CH:16]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1>>[CH2:24]([NH:23][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])[CH3:25]

Participants

5

Reactant 4

HCID 4034-AminophenolHCID 6341EthylamineHCID 110951464-chloropyridine-2-carbonyl ChlorideHCID 228321314-chloro-N-ethylpyridine-2-carboxamide

Product 1

HCID 236145594-(2-(N-ethylcarbamoyl)-4-pyridyloxy)aniline

Procedure

Entry 19: 4-Chloropyridine-2-carbonyl chloride was reacted with ethylamine according to Method A2, Step 3b. The resulting 4-chloro-N-ethyl-2-pyridinecarboxamide was reacted with 4-aminophenol according to Method A2, Step 4 to give 4-(2-(N-ethylcarbamoyl)-4-pyridyloxy)aniline. 5-(Trifluoromethyl)-2-methoxyaniline was converted into 5-(trifluoromethyl)-2-methoxyphenyl isocyanate according to Method B1. 5-(Trifluoromethyl)-2-methoxyphenyl isocyanate was reacted with 4-(2-(N-ethylcarbamoyl)-4-pyridyloxy)aniline according to Method C1a to afford the urea.

Sources & evidence

ORD record
ord-8ddab0d1f73c4c06aa63026eb3d9f64d
Source dataset
uspto-grants-2014_09
Patent number
US08841330B2

Linked notes

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