3-Phenylpropylamine → N-{3-oxo-3-[4-(pyridin-2-yl)piperazin-1-yl]propyl}-1,3-dihydro-2H-isoindole-2-carboxamide
Reaction equation
C1(CCC[NH2:10])C=CC=CC=1.[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][N:12]1[C:20]([NH:22][CH2:23][CH2:24][C:25]([OH:27])=O)=[O:21].[CH2:28]1[C:36]2[C:31](=CC=CC=2)[CH2:30][N:29]1[C:37]([NH:39][C:40]1[CH:48]=[CH:47][C:43](C(O)=O)=CC=1)=O>>[O:27]=[C:25]([N:10]1[CH2:36][CH2:28][N:29]([C:37]2[CH:43]=[CH:47][CH:48]=[CH:40][N:39]=2)[CH2:30][CH2:31]1)[CH2:24][CH2:23][NH:22][C:20]([N:12]1[CH2:11][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)=[O:21]Participants
4
Procedure
The title compound was prepared as described in Example 1C, substituting 1-(pyridin-2-yl)piperazine for 3-phenylpropan-1-amine and 3-(isoindoline-2-carboxamido)propanoic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.11 (ddd, J=4.9, 2.0, 0.8 Hz, 1H), 7.53 (ddd, J=8.7, 7.0, 1.9 Hz, 1H), 7.25-7.34 (m, 4H), 6.83 (d, J=8.6 Hz, 1H), 6.65 (ddd, J=7.1, 4.9, 0.8 Hz, 1H), 6.37 (t, J=5.6 Hz, 1H), 4.57 (s, 4H), 3.44-3.61 (m, 8H), 3.28-3.37 (m, 2H), 2.54-2.61 (m, 2H); MS (ESI(+)) m/e 380 (M+H)+.
Sources & evidence
- ORD record
- ord-830852b5e48b419da9c796d3766f5447
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302989B2
Reaction notes
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