2,5-Dichloro-1,8-naphthyridine → 4-[2-(7-Chloro-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenol

HRID 883879Notes

Reaction equation

HRID 883879 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2Cl)[N:3]=1.[NH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[S:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:9]([C:8]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=3[S:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)=[CH:7][CH:6]=[N:5]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 155883162,5-Dichloro-1,8-naphthyridineHCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 866154844-[2-(7-Chloro-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 21d (0.67 g, 3.36 mmol) and the product from Example 9c (0.78 g, 3.36 mmol) in 10 mL ethanol were heated under reflux for 5.5 hr. The reaction mixture was cooled to room temperature and the solvent was removed concentrated under vacuum leaving yellow solid that was used without further purification (1.43 g, 100%).

Workup

  1. temperatureunder reflux for 5.5 hr
  2. customthe solvent was removed
  3. concentrationconcentrated under vacuum
  4. customleaving yellow solid that
  5. customwas used without further purification (1.43 g, 100%)

Sources & evidence

ORD record
ord-f358fe524d6f408a9e59bfaa1959b965
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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