2-(4-Methoxy-phenylsulfanyl)-5-methyl-phenylamine → (7-Ethyl-[1,8]naphthyridin-4-yl)-[2-(4-methoxy-phenylsulfanyl)-5-methyl-phenyl]-amine

HRID 2358728Notes

Reaction equation

HRID 2358728 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH3:13])=[N:7]2.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[NH2:30])=[CH:18][CH:17]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:30][C:24]3[CH:25]=[C:26]([CH3:29])[CH:27]=[CH:28][C:23]=3[S:22][C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH3:13]

Participants

3

Reactant 2

HCID 433496162-(4-Methoxy-phenylsulfanyl)-5-methyl-phenylamineHCID 672512035-Chloro-2-ethyl-1,8-naphthyridine

Product 1

HCID 68460864(7-Ethyl-[1,8]naphthyridin-4-yl)-[2-(4-methoxy-phenylsulfanyl)-5-methyl-phenyl]-amineYield 98.4%

Procedure

The product from Example 3f (79 mg, 0.41 mmol) was reacted with the product from Example 50b (88 mg, 0.41 mmol) for 23 h giving following the procedure from Example 1g providing the crude title compound that was triturated with 3:1 ether/THF to give the title compound (162 mg, 90%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.37 (t, J=7.35 Hz, 3 H) 2.34 (s, 3 H) 3.05 (q, J=7.35 Hz, 2 H) 3.72 (s, 3 H) 6.27 (d, J=6.98 Hz, 1 H) 6.85 (m, J=8.82 Hz, J=2.20 Hz, 2 H) 7.10 (d, J=8.09 Hz, 1 H) 7.23-7.32 (m, 4 H) 7.83 (d, J=8.83 Hz, 1 H) 8.41 (d, J=6.98 Hz, 1 H) 9.11 (d, J=8.83 Hz, 1 H) 11.16 (br s, 1 H) 14.39 (br s, 1 H); MS (ESI+) m/z 402 (M−Cl)+; (ESI−) m/z 400 (M−HCl)−.

Workup

  1. customgiving
  2. customproviding the crude title compound that
  3. customwas triturated with 3:1 ether/THF

Sources & evidence

ORD record
ord-2831b79632474f76b7d5de13f6a4949e
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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