3-Phenylpropylamine → HCID 178523828, compound

HRID 624289Notes

Reaction equation

HRID 624289 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[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](O)=[O:28])[CH2:24]1)=[O:21].C1C2C(=CC=CC=2)CN1C(NC1C=CC(C(O)=O)=CC=1)=O>>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][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:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

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

Product 1

HCID 178523828HCID 178523828, compound

Procedure

The title compound was prepared as described in Example 1C, substituting 3-phenylpropylamine 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), 7.75 (t, J=5.5 Hz, 1H), 7.38 (d, J=5.1 Hz, 1H), 7.32-7.24 (m, 2H), 7.24-7.13 (m, 3H), 6.58 (d, J=7.6 Hz, 1H), 4.66-4.55 (m, 4H), 4.41-4.27 (m, 1H), 3.11-3.03 (m, 2H), 2.89-2.75 (m, 1H), 2.62-2.52 (m, 2H), 2.39-2.25 (m, 2H), 2.26-2.11 (m, 2H), 1.76-1.63 (m, 2H); MS (ESI(+)) m/e 379 (M+H)+.

Sources & evidence

ORD record
ord-7c65f0d23de24e269fbdaf83d5b8b7c6
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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