5-Methyl-2-phenylsulfanyl-phenylamine → (7-Ethyl-[1,8]naphthyridin-4-yl)-(5-methyl-2-phenylsulfanyl-phenyl)-amine
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][C:15]1[CH:16]=[CH:17][C:18]([S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([NH2:21])[CH:20]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:21][C:19]3[CH:20]=[C:15]([CH3:14])[CH:16]=[CH:17][C:18]=3[S:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH3:13]Participants
3
Procedure
The product from Example 3f (88 mg, 0.46 mmol) was reacted with the product from Example 1f (100 mg, 0.46 mmol) for 24 h following the procedure from Example 1f giving the title compound as a hydrochloride salt which was triturated with ether giving (134 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (t, J=7.35 Hz, 3H) 3.02 (q, J=7.35 Hz, 2H) 6.69 (d, J=6.99 Hz, 1H) 6.97 (d, J=8.82 Hz, 2H) 7.10 (dd, J=7.35 Hz, 1H) 7.15 (d, J=8.82 Hz, 2H) 7.30 (dd, J=8.09 Hz, J=7.72 Hz, 2H) 7.56 (dd, J=2.94 Hz, J=9.19 Hz, 1H) 7.71 (d, J=2.57 Hz, 1H) 7.88 (d, J=8.82 Hz, 1H) 8.52 (d, J=6.99 Hz, 1H) 9.02 (d, J=8.45 Hz, 1H) 11.16 (br s, 1H) 14.56 (br s, 1H); MS (ESI+) m/z 376 (M−Cl)+; (ESI−) m/z 374 (M−HCl)−.
Sources & evidence
- ORD record
- ord-9c98d3aebdd54d2bba1408c81de9d5aa
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338605B2
Reaction notes
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