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

HRID 2197727Notes

Reaction equation

HRID 2197727 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-304c30e98aec4607922041a12c9253fc
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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