3-Phenylpropylamine → N-(5-{[4-(pyridin-2-yl)piperazin-1-yl]carbonyl}pyridin-2-yl)-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624151Notes

Reaction equation

HRID 624151 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][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](=CC=CC=2)[CH2:34][N:33]1[C:41]([NH:43][C:44]1[CH:52]=[CH:51][C:47](C(O)=O)=CC=1)=O>>[N:43]1[CH:44]=[CH:52][CH:51]=[CH:47][C:41]=1[N:33]1[CH2:32][CH2:40][N: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])[CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 62230337HCID 62230337, compoundHCID 687478296-(Isoindoline-2-carboxamido)nicotinic acid

Product 1

HCID 57509984N-(5-{[4-(pyridin-2-yl)piperazin-1-yl]carbonyl}pyridin-2-yl)-1,3-dihydro-2H-isoindole-2-carboxamide

Procedure

The title compound was prepared as described in Example 1C, substituting N-(2-pyridyl)piperazine 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 9.21 (s, 1H), 8.39 (dd, J=2.3, 0.8 Hz, 1H), 8.13 (dd, J=4.9, 1.9 Hz, 1H), 8.00 (dd, J=8.6, 0.8 Hz, 1H), 7.84 (dd, J=8.6, 2.4 Hz, 1H), 7.56 (ddd, J=8.7, 6.9, 1.9 Hz, 1H), 7.34-7.39 (m, 2H), 7.29-7.34 (m, 2H), 6.85 (d, J=8.5 Hz, 1H), 6.67 (dd, J=6.7, 4.9 Hz, 1H), 4.75-4.92 (bs, 4H), 3.47-3.81 (m, 8H); MS (ESI(+)) m/e 429 (M+H)+.

Sources & evidence

ORD record
ord-958fd4303277470e9f90699fcc0a326c
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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