1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1178118Notes

Reaction equation

HRID 1178118 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[CH:17]=[C:18]([C:21]([OH:23])=O)[NH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:46][CH2:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:52][CH2:51]1)=[O:49]>CN(C=O)C.O>[O:49]=[C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:54][CH2:55]1)[CH2:47][NH:46][C:21]([C:18]1[NH:19][CH:20]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=1)=[O:23]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 128971004-phenyl-1H-pyrrole-2-carboxylic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 251655364-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amideYield 87.59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (155 mg, 0.2 mL, 1.19 mmol) was added to a stirred solution of 4-Phenyl-1H-pyrrole-2-carboxylic acid (50 mg, 0.26 mmol) in DMF (4 mL). HOBT (40 mg, 0.29 mmol) and EDCI (153 mg, 0.79 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method as described above) (103 mg, 0.29 mmol) was added and the resulting mixture was stirred at room temperature for 4 hrs. Cold water was then added and filtered the solid precipitated to afford 113 mg (87.59% yield) of 4-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 92.52%. 1H NMR (DMSO-d6): δ 11.6 (s, 1H), 8.2-8.1 (bs, 1H), 7.9-7.72 (m, 2H), 7.7-7.64 (t, 1H), 7.6-7.5 (d, 3H), 7.38-7.28 (t, 3H), 7.24-7.1 (m, 2H), 4.2-4.04 (bd, 2H), 3.82-3.56 (m, 4H), 3.5-3.4 (bs, 2H), 3.2-3.1 (bd, 2H).

Workup

  1. additionwas added
  2. filtrationfiltered the solid
  3. customprecipitated

Sources & evidence

ORD record
ord-a21d5466ba404535b3808dcf5eae7e97
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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