1-(4-Aminopiperidin-1-yl)ethan-1-one → HCID 71534655, compound
Reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:32])=O)=[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].[C:33]([N:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]1)(=[O:35])[CH3:34]>>[C:33]([N:36]1[CH2:41][CH2:40][CH:39]([NH:42][C:30]([C:27]2[CH:28]=[CH:29][C:24]([C:6]3[C:5]([C:3]([OH:2])=[O:4])=[CH:10][C:9]([C:11]4[S:12][CH:13]=[C:14]([C:16]5[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=5)[N:15]=4)=[CH:8][CH:7]=3)=[CH:25][CH:26]=2)=[O:32])[CH2:38][CH2:37]1)(=[O:35])[CH3:34]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-acetylpiperidin-4-amine (available from Aldrich Chemical Company, Inc.; 88 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4′-(1-acetyl-piperidin-4-ylcarbamoyl)-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (5 mg, 4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.19 (br s, 1H), 8.45 (s, 1H), 8.33 (s, 3H), 8.19 (d, J=7.8 Hz, 1H), 8.09 (d, J=8.5 Hz, 1H), 7.90 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.3 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H), 4.35 (d, J=12.3 Hz, 1H), 4.05 (br s, 1H), 3.85 (d, J=13.3 Hz, 1H), 3.16 (t, J=11.8 Hz, 1H), 2.69 (d, J=13.3 Hz, 1H), 2.02 (s, 3H), 1.78-1.93 (m, 1H), 1.18-1.58 (m, 4H).
Workup
- customthe acid was purified
- customHPLC Purification Conditions B
Sources & evidence
- ORD record
- ord-34b70e45d7c94d44b621969f93ff3df8
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073881B2
Reaction notes
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