5-Chloro-2-methyl-1,8-naphthyridine → HCID 16214862, compound

HRID 883844Notes

Reaction equation

HRID 883844 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH2:20])[CH:19]=1>CCO>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:20][C:18]3[CH:19]=[C:14]([CH3:13])[CH:15]=[CH:16][C:17]=3[S:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 433496035-Methyl-2-phenylsulfanyl-phenylamine

Product 1

HCID 16214862HCID 16214862, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of the product from Example 7d (65 mg, 0.36 mmol) and the product from Example 7f (77 mg, 0.36 mmol) in 3 mL of EtOH was heated at 80° C. for 7 h. Concentrated under vacuum. Recrystallized from THF with a few drops of MeOH. Filtration gave the title compound as the hydrochloride salt as a white solid (62 mg, 43%) 1H NMR (300 MHz, CDCl3) δ ppm: 1.62 (brs, 1 H) 2.43 (s, 3 H) 2.52 (s, 3 H) 6.02 (d, J=7.0 Hz, 1 H) 7.05-7.35 (m, 8 H) 7.70 (brs, 1 H) 8.00 (d, J=7.0 Hz, 1 H) 8.85 (d, J=8.5 Hz, 1 H) 10.80 (brs, 1 H); MS (ESI+) m/z 358 (M-Cl)+; (ESI−) m/z 356 (M−HCl)−.

Workup

  1. concentrationConcentrated under vacuum
  2. customRecrystallized from THF with a few drops of MeOH
  3. filtrationFiltration

Sources & evidence

ORD record
ord-940473e3fdf24281901f50b1b92ab683
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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