3-Phenylpropylamine → N-{3-[(3-methylbutyl)amino]-3-oxopropyl}-1,3-dihydro-2H-isoindole-2-carboxamide
Reaction equation
C1(CCCN)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](=[CH:32]C=CC=2)[CH2:30][N:29]1C(NC1C=CC(C(O)=O)=CC=1)=O>>[CH3:30][CH:31]([CH3:32])[CH2:36][CH2:28][NH:29][C:25](=[O:27])[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 1,3-methylbutan-1-amine 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 7.76-7.81 (m, 1H), 7.25-7.34 (m, 4H), 6.31-6.36 (m, 1H), 4.56 (s, 4H), 3.23-3.31 (m, 2H), 3.02-3.09 (m, 2H), 2.27 (t, J=7.0 Hz, 2H), 1.46-1.62 (m, 1H), 1.27 (q, J=7.1 Hz, 2H), 0.84 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 304 (M+H)+.
Sources & evidence
- ORD record
- ord-628a9e578a1b44619e9a6a2c04b6b555
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302989B2
Reaction notes
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