1-Acetylpiperazine → HCID 71537483, compound

HRID 1519311Notes

Reaction equation

HRID 1519311 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][NH:39][CH2:38][CH2:37]1)(=[O:35])[CH3:34]>>[C:33]([N:36]1[CH2:41][CH2:40][N:39]([C:30]([C:27]2[CH:26]=[CH:25][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:29][CH:28]=2)=[O:32])[CH2:38][CH2:37]1)(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 837951-AcetylpiperazineHCID 86679835HCID 86679835, compound2×

Product 1

HCID 71537483HCID 71537483, compoundYield 68%

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-acetylpiperazine (available from Aldrich Chemical Company, Inc.; 79 mg, 0.62 mmol). The resulting ester was hydrolyzed and the acid was purified using HPLC Purification Conditions B to give 4′-(4-acetyl-piperazine-1-carbonyl)-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (81 mg, 68%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.24 (br s, 1H), 8.48 (s, 1H), 8.37 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.24 (dd, J=8.0, 2.0 Hz, 1H), 8.10 (dd, J=8.3, 2.0 Hz, 1H), 7.77 (d, J=8.3 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 7.45-7.53 (m, 4H), 3.46-3.59 (br s, 6H), 3.32-3.36 (s, 6H), 2.03 (s, 3H).

Workup

  1. customthe acid was purified
  2. customHPLC Purification Conditions B

Sources & evidence

ORD record
ord-db9ba4bc544b4754a5d339a7c2ccb8bb
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

Loading…