Ethanol → 4-[4-Phenoxymethyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol
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][CH2:13][CH3:14])=[N:7]2.C(O)C.[NH2:18][C:19]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:21][C:20]=1[S:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1>>[O:26]([CH2:25][C:23]1[CH:22]=[CH:21][C:20]([S:33][C:34]2[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=2)=[C:19]([NH:18][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:24]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
The product from Example 2g as a 4.1M solution in ethanol (0.050 mL, 0.205 mmol) was reacted with the product from Example 221d (0.066 g, 0.205 mmol) for 16.5 h following the procedure from Example 1g. Consumption of starting material required a second addition of the product from Example 2g (0.025 mL, 0.102 mmol) and continued heating at 80° C. (12 h). The crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.0269 g, 21.5%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.54 Hz, 3H) 1.76-1.99 (m, 2H) 3.00 (t, J=7.35 Hz, 2H) 5.12 (s, 2H) 6.31 (d, J=6.99 Hz, 1H) 6.79 (d, J=8.82 Hz, 2H) 6.91-7.07 (m, 4H) 7.17-7.37 (m, 4H) 7.43-7.55 (m, 2H) 7.84 (d, J=8.82 Hz, 1H) 8.47 (d, J=7.35 Hz, 1H) 9.04 (d, J=8.46 Hz, 1H) 9.97 (s, 1H); MS (ESI+) m/z 494.2 (M+H)+; (ESI−) m/z 492.2 (M−H)−.
Workup
- customConsumption of starting material
- customThe crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.0269 g, 21.5%)
Sources & evidence
- ORD record
- ord-6d090fa26ce743adb8e9bfff38aab8ea
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338605B2
Reaction notes
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