3-Phenylpropylamine → HCID 178523827, compound

HRID 624288Notes

Reaction equation

HRID 624288 reaction equation
[C:1]1([CH2:7][CH2:8]CN)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH2:13][N:12]1[C:20]([NH:22][C@H:23]1[CH2:26][C@H:25]([C:27]([OH:29])=O)[CH2:24]1)=[O:21].C1C2C(=CC=CC=2)C[N:31]1C(NC1C=CC(C(O)=O)=CC=1)=O>>[C:1]1([CH2:7][CH2:8][NH:31][C:27]([C@H:25]2[CH2:26][C@H:23]([NH:22][C:20]([N:12]3[CH2:11][C:19]4[CH:18]=[CH:17][N:16]=[CH:15][C:14]=4[CH2:13]3)=[O:21])[CH2:24]2)=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 62230337HCID 62230337, compoundHCID 178523829HCID 178523829, compound

Product 1

HCID 178523827HCID 178523827, compound

Procedure

The title compound was prepared as described in Example 1C, substituting 2-phenylethylamine for 3-phenylpropan-1-amine and trans-3-(2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-2-carboxamido)cyclobutanecarboxylic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.56 (s, 1H), 8.47 (d, J=5.0 Hz, 1H), 7.80 (t, J=5.6 Hz, 1H), 7.39 (d, J=5.1 Hz, 1H), 7.33-7.24 (m, 2H), 7.23-7.16 (m, 3H), 6.57 (d, J=7.6 Hz, 1H), 4.65-4.58 (m, 4H), 4.38-4.24 (m, 1H), 3.33-3.23 (m, 2H), 2.84-2.74 (m, 1H), 2.72 (t, J=7.3 Hz, 2H), 2.32-2.22 (m, 2H), 2.24-2.09 (m, 2H); MS (ESI(+)) m/e 365 (M+H)+.

Sources & evidence

ORD record
ord-3d45b7d498d248348d2db45fa8b378c7
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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