3-Phenylpropylamine → HCID 57510308, compound

HRID 624221Notes

Reaction equation

HRID 624221 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])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:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=1)=[O:21].C1C2C(=CC=CC=2)CN1[C:41](NC1C=CC(C(O)=O)=CC=1)=[O:42]>>[O:42]1[CH2:1][CH2:7][C@@H:8]([CH2:9][NH:10][C:27]([C:26]2[CH:30]=[CH:31][C: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])=[CH:24][CH:25]=2)=[O:29])[CH2:41]1

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 62230337HCID 62230337, compoundHCID 68748914HCID 68748914, compound

Product 1

HCID 57510308HCID 57510308, compound

Procedure

The title compound was prepared as described in Example 1C, substituting (S)-(tetrahydrofuran-3-yl)methanamine for 3-phenylpropan-1-amine and 4-(2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-2-carboxamido)benzoic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (300 MHz, DMSO-d6) δ 8.64 (s, 2H), 8.61 (s, 1H), 8.50 (d, J=5.0 Hz, 1H), 8.38 (t, J=5.7 Hz, 1H), 7.81-7.74 (m, 2H), 7.69-7.62 (m, 2H), 7.44 (d, J=5.1 Hz, 1H), 4.86-4.79 (m, 4H), 3.80-3.66 (m, 2H), 3.67-3.56 (m, 1H), 3.47 (dd, J=8.5, 5.3 Hz, 1H), 3.21 (dt, J=13.2, 5.8 Hz, 1H), 2.01-1.86 (m, 1H), 1.67-1.53 (m, 1H); MS (ESI(+)) m/e 367 (M+H)+.

Sources & evidence

ORD record
ord-af4a7d6ed5df43fe9cd759176a975d25
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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