N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide → N-{4-[2-(7-Ethyl-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenyl}-acetamide
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.[NH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[S:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:14][C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=3[S:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:32])[CH3:31])=[CH:25][CH:24]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH3:13]Participants
3
Procedure
The product from Example 3f (92 mg, 0.47 mmol) was reacted with the product from Example 18b (130 mg, 0.47 mmol) for 22 h following the procedure from Example 1g giving the title compound as a solid after purification of the crude product by HPLC with TFA as a trifluoroacetic acid salt (68 mg, 26%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.37 (t, J=7.72 Hz, 1H) 2.04 (s, 3H) 2.35 (s, 3H) 3.05 (q, J=7.72 Hz, 2H) 6.31 (d, J=6.98 Hz, 1H) 7.15 (d, J=8.83 Hz, 1H) 7.20-7.35 (m, 3H) 7.49 (d, J=8.83 Hz, 2H) 7.82 (d, J=8.82 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.82 Hz, 1H) 10.04 (s, 1H) 11.01 (br s, 1H) 14.39 (br s, 1H). MS (ESI+) m/z 429 (M+H−Cl)+; (ESI−) m/z 427 (M−H−Cl)−.
Sources & evidence
- ORD record
- ord-e70c04db80954ab39ccbe324b0e426df
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338605B2
Reaction notes
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