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

HRID 2078625Notes

Reaction equation

ClC1C=CN=C(C(Cl)=O)C=1.C(N)(C)C.Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:17]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1>>[CH:25]([NH:24][C:22]([C:18]1[CH:17]=[C:16]([O:35][C:32]2[CH:33]=[CH:34][C:29]([NH2:28])=[CH:30][CH:31]=2)[CH:21]=[CH:20][N:19]=1)=[O:23])([CH3:27])[CH3:26]

Participants

Reactant 4

HCID 4034-Aminophenol

HCID 6363Isopropylamine

HCID 110951464-chloropyridine-2-carbonyl Chloride

HCID 228320834-Chloro-N-isopropyl-pyridine-2-carboxamide

Product 1

HCID 236145604-(2-(N-isopropylcarbamoyl)-4-pyridyloxy)aniline

Procedure

Entry 100: 4-Chloropyridine-2-carbonyl chloride was reacted with isopropylamine according to Method A2, Step 3b. The resulting 4-chloro-N-isopropyl-2-pyridinecarboxamide was reacted with 4-aminophenol according to Method A2, Step 4 to give 4-(2-(N-isopropylcarbamoyl)-4-pyridyloxy)aniline. 4-Chloro-2-methoxy-5-(trifluoromethyl)aniline was synthesized according to Method A7. 4-Chloro-2-methoxy-5-(trifluoromethyl)aniline was converted into 4-chloro-2-methoxy-5-(trifluoromethyl)phenyl isocyanate according to Method B 1. According to Method C1a, 4-chloro-2-methoxy-5-(trifluoromethyl)phenyl isocyanate was reacted with 4-(2-(N-isopropylcarbamoyl)-4-pyridyloxy)aniline afford the urea.

Sources & evidence

ORD record: ord-f61c041078a047fe9c67e9eb02ab7aa0
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928239B2

Reaction notes

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