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

HRID 2358562Notes

Reaction equation

HRID 2358562 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 13d (0.67 g, 3.36 mmol) and the product from Example 4c (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-1d9c04ed59604d0ca91d6e1af27f3ceb
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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