2-(Pyridin-3-yl)ethan-1-amine → HCID 71538601, compound
Reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:24]2[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[CH:26][CH:25]=2)=[CH:7][CH:8]=[C:9]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[N:15]=2)[CH:10]=1)=[O:4].[NH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1>>[Cl:23][C:18]1[CH:17]=[C:16]([C:14]2[N:15]=[C:11]([C:9]3[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:31])[NH:33][CH2:34][CH2:35][C:36]5[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=5)=[CH:26][CH:25]=4)=[CH:7][CH:8]=3)[S:12][CH:13]=2)[CH:21]=[CH:20][C:19]=1[Cl:22]Participants
Procedure
Using the conditions of General Procedure E for Amide Coupling in Parallel Mode, 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (which may be prepared as described for Intermediate 8; 100 mg, 0.21 mmol) was reacted with 3-(2-aminoethyl)pyridine (available from Aldrich Chemical Company, Inc.; 76 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-4′-(2-pyridin-3-yl-ethylcarbamoyl)-biphenyl-2-carboxylic acid (129 mg, 109%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.14 (br s, 1H), 8.63 (t, J=5.5 Hz, 1H), 8.57 (s, 1H), 8.51 (d, J=4.3 Hz, 1H), 8.47 (s, 1H), 8.39 (d, J=1.8 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.24 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.4, 1.9 Hz, 1H), 7.83-7.90 (m, 3H), 7.76 (d, J=8.3 Hz, 1H), 7.58 (d, J=8.3 Hz, 1H), 7.45-7.52 (m, 3H), 3.58 (q, J=6.6 Hz, 2H), 2.95 (t, J=6.9 Hz, 7H).
Workup
- customthe acid was purified
- customHPLC Purification Conditions B
Sources & evidence
- ORD record
- ord-f5085eb47eaa45f5b61d35d54df88296
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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