3-Phenylpropylamine → HCID 86665077, compound

HRID 624178Notes

Reaction equation

HRID 624178 reaction equation
C1(C[CH2:8][CH2:9][NH2:10])C=CC=CC=1.[CH2:11]([NH:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([N:26]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[C:31]([C:35](O)=[O:36])[CH:32]=3)[CH2:27]2)=[O:25])=[CH:19][CH:18]=1)=[O:16])[CH2:12][CH3:13].C1C2C(=CC=CC=2)CN1[C:47](NC1C=CC(C(O)=O)=CC=1)=[O:48]>>[CH3:47][O:48][CH2:8][CH2:9][NH:10][C:35]([C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[CH2:27][N:26]([C:24]([NH:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([NH:14][CH2:11][CH2:12][CH3:13])=[O:16])=[CH:18][CH:19]=1)=[O:25])[CH2:34]2)=[O:36]

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 57509897HCID 57509897, compoundHCID 62230337HCID 62230337, compound

Product 1

HCID 86665077HCID 86665077, compound

Procedure

The title compound was prepared as described in Example 1C, substituting 2-methoxyethanamine for 3-phenylpropan-1-amine and 2-{[4-(propylcarbamoyl)phenyl]carbamoyl}isoindoline-5-carboxylic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.61 (s, 1H), 8.54 (d, J=5.3 Hz, 1H), 8.26 (t, J=5.7 Hz, 1H), 7.79-7.85 (m, 2H), 7.73-7.80 (m, 2H), 7.63-7.67 (m, 2H), 7.45 (d, J=7.8 Hz, 1H), 4.81-4.83 (bs, 4H), 3.39-3.51 (m, 4H), 3.27 (s, 3H), 3.03-3.22 (m, 2H), 1.46-1.59 (m, 2H), 0.89 (t, J=7.4 Hz, 3H); MS (ESI(+)) m/e 425 (M+H)+.

Sources & evidence

ORD record
ord-344b68e9ce88489ab6dbd7ce9de0c1f4
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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