3-Phenylpropylamine → N-{5-[(3-methylbutyl)carbamoyl]pyridin-2-yl}-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][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][N:24]=1)=[O:21].[CH2:32]1[C:40]2[C:35](=[CH:36]C=CC=2)[CH2:34][N:33]1C(NC1C=CC(C(O)=O)=CC=1)=O>>[CH3:34][CH:35]([CH3:36])[CH2:40][CH2:32][NH:33][C:27]([C:26]1[CH:30]=[CH:31][C:23]([NH:22][C:20]([N:12]2[CH2:11][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:21])=[N:24][CH:25]=1)=[O:29]Participants
4
Procedure
The title compound was prepared as described in Example 1C, substituting 3-methylbutan-1-amine for 3-phenylpropan-1-amine and 6-(isoindoline-2-carboxamido)nicotinic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1H), 8.73 (d, J=2.4 Hz, 1H), 8.42 (t, J=5.5 Hz, 1H), 8.13 (dd, J=8.8, 2.4 Hz, 1H), 7.99 (d, J=8.7 Hz, 1H), 7.25-7.37 (m, 4H), 4.71-4.95 (bs, 4H), 3.24-3.32 (m, 2H), 1.57-1.68 (m, 1H), 1.43 (q, J=7.1 Hz, 2H), 0.91 (d, J=6.6 Hz, 6H); MS (ESI(+)) m/e 353 (M+H)+.
Sources & evidence
- ORD record
- ord-98061d7f224c405ea051ffc4af1acdbc
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302989B2
Reaction notes
Loading…