1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1178115Notes

Reaction equation

HRID 1178115 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][C:19]([C:21]([OH:23])=O)=[CH:18][CH:17]=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:19]1[NH:20][C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:17][CH:18]=1)=[O:23]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2261995-phenyl-1H-pyrrole-2-carboxylic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 251655355-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amideYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (102 mg, 0.14 mL, 0.79 mmol) was added to a stirred solution of 5-phenyl-1H-pyrrole-2-carboxylic acid (37 mg, 0.19 mmol) in DMF (4 mL). HOBT (30 mg, 0.22 mmol) and EDCI (57 mg, 0.29 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) (83.6 mg, 0.23 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 69 mg (72% yield) of 5-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 89.78%. 1H NMR (DMSO-d6): δ 11.7 (s, 1H), 8.2-8.1 (bs, 1H), 7.9-7.7 (s, 4H), 7.7-7.6 (s, 1H), 7.6-7.5 (s, 1H), 7.45-7.3 (t, 2H), 7.3-7.2 (t, 1H), 6.9-6.8 (s, 1H), 6.6-6.5 (s, 1H), 4.28-4.04 (d, 2H), 3.84-3.5 (bs, 4H), 3.5-3.4 (s, 2H), 3.2-3.0 (d, 2H).

Workup

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

Sources & evidence

ORD record
ord-bdd16a69a3814a41b81b453ed1895f56
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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