3-Aminophenol → 4-(3-Aminophenoxy)pyridine-2-carboxamide

HRID 598469Notes

Reaction equation

HRID 598469 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH2:10])=[O:9])[CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1>CN(C=O)C>[C:8]([C:4]1[CH:3]=[C:2]([O:18][C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=2)[NH2:11])[CH:7]=[CH:6][N:5]=1)(=[O:9])[NH2:10]

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 3035434-Chloropyridine-2-carboxamide

Product 1

HCID 231372294-(3-Aminophenoxy)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Entry 12: 4-Chloropyridine-2-carbonyl chloride HCl salt was reacted with ammonia according to Method A2, Step 3b to form 4-chloro-2-pyridinecarboxamide. 4-Chloro-2-pyridinecarboxamide was reacted with 3-aminophenol according to Method A2, Step 4 using DISC in place of DMF to give 3-(2-carbamoyl-4-pyridyloxy)aniline. According to Method C2a, 2-methoxy-5-(trifluoromethyl)aniline was reacted with phosgene followed by 3-(2-carbamoyl-4-pyridyloxy)aniline to afford the urea.

Sources & evidence

ORD record
ord-9c24e31243cb432f975a6a4e5cd48f8d
Source dataset
uspto-grants-2011_03
Patent number
US07897623B2

Reaction notes

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