2-Morpholinoethylamine → 4-(4-Benzylphenylamino)-6-(2-morpholinoethylamino)-1,7-naphthyridine-3-carbonitrile
Reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:10]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][N:30]=[C:31](F)[CH:32]=3)[N:27]=[CH:26][C:25]=2[C:35]#[N:36])=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([C:17]1[CH:18]=[CH:19][C:20]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][N:30]=[C:31]([NH:1][CH2:2][CH2:3][N:4]4[CH2:9][CH2:8][O:7][CH2:6][CH2:5]4)[CH:32]=3)[N:27]=[CH:26][C:25]=2[C:35]#[N:36])=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Procedure
Following the procedure described above in Example 1,4-(4-benzylphenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.675 g, 1.90 mmol) was reacted with 4-(2-aminoethyl)morpholine (5.0 mL, 5.0 g, 38 mmol). This process was repeated with three additional aliquots of 4-(4-benzylphenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile (0.62 g, 0.62 g, 0.30 g). The contents of all four tubes were worked up together, and the crude product purified by flash chromatography over silica gel (5-6% MeOH in CH2Cl2) to give pure product as bright yellow crystals (1.17 g, 40% yield): 1H NMR (400 MHz, DMSO-D6) δ 2.43 (br s, 4 H) 2.56 (t, J=6.7 Hz, 2 H) 3.31-3.39 (m, 2 H) 3.50-3.66 (m, 4 H) 3.99 (s, 2 H) 6.58 (t, J=4.9 Hz, 1 H) 7.04 (s, 1 H) 7.13-7.35 (m, 9 H) 8.22 (s, 1 H) 8.82 (s, 1 H) 9.56 (s, 1 H); HRMS (ESI+) calcd for C28H29N6O (MH+) 465.2398, found 465.2396.
Workup
- customthe crude product purified by flash chromatography over silica gel (5-6% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-32761059932240c9bf541ed9885630cc
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432279B2
Reaction notes
Loading…