3-Phenylpropylamine → HCID 178523826, compound

HRID 624287Notes

Reaction equation

HRID 624287 reaction equation
C1(CCCN)C=CC=CC=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].[CH2:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)C[N:31]1C(NC1C=CC(C(O)=O)=CC=1)=O>>[CH2:30]([NH:31][C:27]([C@H:25]1[CH2:24][C@H:23]([NH:22][C:20]([N:12]2[CH2:11][C:19]3[CH:18]=[CH:17][N:16]=[CH:15][C:14]=3[CH2:13]2)=[O:21])[CH2:26]1)=[O:29])[C:38]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 3

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

Product 1

HCID 178523826HCID 178523826, compound

Procedure

The title compound was prepared as described in Example 1C, substituting benzylamine 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), 8.26 (t, J=5.9 Hz, 1H), 7.39 (d, J=5.1 Hz, 1H), 7.36-7.28 (m, 2H), 7.27-7.20 (m, 3H), 6.60 (d, J=7.6 Hz, 1H), 4.65-4.59 (m, 4H), 4.45-4.29 (m, 1H), 4.28 (d, J=5.9 Hz, 2H), 2.96-2.84 (m, 1H), 2.41-2.29 (m, 2H), 2.30-2.15 (m, 2H); MS (ESI(+)) m/e 351 (M+H)+.

Sources & evidence

ORD record
ord-7d66b5c606974751a3e78a4f56c5d75e
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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