3-Phenylpropylamine → N-[6-(methylamino)-6-oxohexyl]-1,3-dihydro-2H-isoindole-2-carboxamide

HRID 624146Notes

Reaction equation

HRID 624146 reaction equation
C1(CC[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][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=O)=[O:21].C1C2C(=CC=CC=2)CN1C(NC1C=CC(C(O)=O)=CC=1)=O>>[CH3:9][NH:10][C:28](=[O:30])[CH2:27][CH2:26][CH2:25][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

Reactant 3

HCID 162593-PhenylpropylamineHCID 62230337HCID 62230337, compoundHCID 622323586-[(1,3-dihydro-2H-isoindol-2-ylcarbonyl)amino]hexanoic acid

Product 1

HCID 57509981N-[6-(methylamino)-6-oxohexyl]-1,3-dihydro-2H-isoindole-2-carboxamide

Procedure

The title compound was prepared as described in Example 1C, substituting methylamine for 3-phenylpropan-1-amine and 6-[(1,3-dihydro-2H-isoindol-2-ylcarbonyl)amino]hexanoic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.60-7.72 (m, 1H), 7.25-7.33 (m, 4H), 6.24-6.29 (m, 1H), 4.57 (s, 4H), 2.94-3.09 (m, 2H), 2.54 (d, J=4.6 Hz, 3H), 2.30 (t, J=7.3 Hz, 1H), 2.04 (t, J=7.4 Hz, 1H), 1.37-1.58 (m, 4H), 1.18-1.35 (m, 2H); MS (ESI(+)) m/e 290 (M+H)+.

Sources & evidence

ORD record
ord-555653767a48432599116d5ec8af439b
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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