(1-Methyl-1H-pyrazol-5-yl)methanamine → HCID 71534656, 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].[CH3:33][N:34]1[C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=[N:35]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:40][CH2:39][C:38]5[N:34]([CH3:33])[N:35]=[CH:36][CH:37]=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 (1-methyl-1H-pyrazol-5-yl)methylamine (available from Aldrich Chemical Company, Inc.; 69 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-methyl-2H-pyrazol-3-ylmethyl)-carbamoyl]-biphenyl-2-carboxylic acid (100 mg, 86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.23 (br s, 1H), 9.07 (t, J=5.6 Hz, 1H), 8.48 (s, 1H), 8.38 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.24 (dd, J=8.0, 1.8 Hz, 1H), 8.10 (dd, J=8.4, 1.9 Hz, 1H), 7.94 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.32 (d, J=1.8 Hz, 1H), 6.19 (d, J=1.5 Hz, 1H), 4.55 (d, J=5.5 Hz, 2H), 3.84 (s, 3H).
Workup
- customthe acid was purified
- customHPLC Purification Conditions B
Sources & evidence
- ORD record
- ord-748c3768cb894786bbf8c399cad2ec70
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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