3-Phenylpropylamine → HCID 57509988, compound

HRID 624153Notes

Reaction equation

HRID 624153 reaction equation
C1(CCCN)C=CC=CC=1.[CH2:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][N:12]1[C:20]([NH:22][C:23]1[S:24][C:25]([C:28]([OH:30])=O)=[CH:26][N:27]=1)=[O:21].[CH2:31]1[C:39]2[C:34](=[CH:35]C=CC=2)[CH2:33][N:32]1C(NC1C=CC(C(O)=O)=CC=1)=O>>[CH3:33][CH:34]([CH3:35])[CH2:39][CH2:31][NH:32][C:28]([C:25]1[S:24][C:23]([NH:22][C:20]([N:12]2[CH2:11][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13]2)=[O:21])=[N:27][CH:26]=1)=[O:30]

Participants

4

Reactant 3

HCID 162593-PhenylpropylamineHCID 62230337HCID 62230337, compoundHCID 86665075HCID 86665075, compound

Product 1

HCID 57509988HCID 57509988, compound

Procedure

The title compound was prepared as described in Example 1C, substituting 3-methylbutan-1-amine for 3-phenylpropan-1-amine and 2-(isoindoline-2-carboxamido)thiazole-5-carboxylic acid for 4-(isoindoline-2-carboxamido)benzoic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.01-11.16 (bs, 1H), 8.27 (t, J=5.6 Hz, 1H), 7.96 (s, 1H), 7.29-7.36 (m, 4H), 4.73-4.88 (bs, 4H), 3.18-3.28 (m, 2H), 1.52-1.69 (m, 1H), 1.34-1.44 (m, 2H), 0.90 (d, J=6.6 Hz, 6H); MS (ESI(−)) m/e 357 (M−H)−.

Sources & evidence

ORD record
ord-fd28682fed5d40b88775e0111ed63693
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

Loading…