1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178489296, compound

HRID 1178143Notes

Reaction equation

HRID 1178143 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[NH:22][N:21]=[C:20]([C:23]([NH:25][CH2:26][C:27]([OH:29])=O)=[O:24])[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[N:52]1([C:58]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:68])[F:67])=[O:59])[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1>CN(C=O)C.O>[O:29]=[C:27]([N:55]1[CH2:56][CH2:57][N:52]([C:58](=[O:59])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:66]([F:69])([F:67])[F:68])[CH2:53][CH2:54]1)[CH2:26][NH:25][C:23]([C:20]1[CH:19]=[C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH3:10])[NH:22][N:21]=1)=[O:24]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 178489298HCID 178489298, compound

Product 1

HCID 178489296HCID 178489296, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (99 mg, 0.13 mL, 0.76 mmol) was added to a stirred solution of {[5-(2-methoxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (60 mg, 0.21 mmol) in DMF (2 mL). HOBT (34 mg, 0.25 mmol) and EDCI (49 mg, 0.25 mmol) were then added at room temperature. After 2 minutes, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride salt (64.3 mg, 0.21 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 40 mg (35.7% yield) of 5-(2-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.45%. 1H NMR (DMSO-d6): δ 13.5 (s, 1H), 8.0 (m, 1H), 7.62 (m, 4H), 7.5 (m, 1H), 7.3 (m, 1H), 7.16 (m, 1H), 7.01 (m, 2H), 4.1 (d, 2H), 3.84 (s, 3H), 3.6 (m, 2H), 3.56 (m, 2H), 3.36 (m, 2H), 3.1 (m, 2H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated

Sources & evidence

ORD record
ord-0689881f93604c33b458f0cab6b887be
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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