3-Phenylpropylamine → N-(5-{[(3S)-tetrahydrofuran-3-ylmethyl]carbamoyl}pyridin-2-yl)-1,3-dihydro-2H-isoindole-2-carboxamide
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][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][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][N:24]=1)=[O:21].C1C2C(=CC=CC=2)CN1[C:41](NC1C=CC(C(O)=O)=CC=1)=[O:42]>>[O:42]1[CH2:1][CH2:7][C@@H:8]([CH2:9][NH:10][C:27]([C:26]2[CH:30]=[CH:31][C:23]([NH:22][C:20]([N:12]3[CH2:11][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13]3)=[O:21])=[N:24][CH:25]=2)=[O:29])[CH2:41]1Participants
4
Procedure
The title compound was prepared as described in Example 1C, substituting (S)-benzyl (tetrahydrofuran-3-yl)methylcarbamate for 3-phenylpropan-1-amine and 6-(isoindoline-2-carboxamido)nicotinic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.27 (s, 1H), 8.74 (d, J=2.1 Hz, 1H), 8.60 (t, J=5.7 Hz, 1H), 8.14 (dd, J=8.8, 2.4 Hz, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.41-7.27 (m, 4H), 4.89 (m, 4H), 3.75 (m, 1H), 3.69 (m, 1H), 3.62 (m, 1H), 3.48 (dd, J=8.5, 5.3 Hz, 1H), 3.25 (m, 2H), 2.48 (m, 1H), 1.95 (m, 1H), 1.61 (m, 1H); MS (ESI(+)) m/e 367 (M+H).
Sources & evidence
- ORD record
- ord-273866a40361498195ec2d53b5ac32a1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302989B2
Reaction notes
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