8-Hydroxyquinoline-7-carboxylic Acid → N-[5-(3-chlorophenyl)-4-oxo-1,3-thiazol-2-yl]-8-hydroxyquinoline-7-carboxamide

HRID 322997Notes

Reaction equation

HRID 322997 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH2:15][C:16]1[S:17][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[C:19]([OH:21])[N:20]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[Cl:28][C:24]1[CH:23]=[C:22]([CH:18]2[S:17][C:16]([NH:15][C:12]([C:3]3[C:2]([OH:1])=[C:11]4[C:6]([CH:7]=[CH:8][CH:9]=[N:10]4)=[CH:5][CH:4]=3)=[O:14])=[N:20][C:19]2=[O:21])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183726302-Amino-5-(3-chlorophenyl)-4-hydroxy-1,3-thiazole

Product 1

HCID 178522601N-[5-(3-chlorophenyl)-4-oxo-1,3-thiazol-2-yl]-8-hydroxyquinoline-7-carboxamideYield 30.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-hydroxyquinoline-7-carboxylic acid (0.284 g) of Preparation 1 and 2-amino-5-(3-chlorophenyl)-4-hydroxy-1,3-thiazole (0.340 g) in 20 mL DMF is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.305 g) and 1-hydroxybenzotriazole monohydrate (0.217 g). The mixture is stirred at room temperature for 7 days. The solution is then poured into 30 mL ice-water. The resulting solid is collected and dried. The crude product is triturated with hot EtOAc, then with hot i-PrOH to yield 0.182 g of the title product as a yellow solid.

Workup

  1. customThe resulting solid is collected
  2. customdried
  3. customThe crude product is triturated with hot EtOAc

Sources & evidence

ORD record
ord-9d1f2101e04c4c22ae46ec6adc5e0c49
Source dataset
uspto-grants-2001_04
Patent number
US06211376B1

Reaction notes

Loading…