1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178489297, compound

HRID 1178140Notes

Reaction equation

HRID 1178140 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]([OH:25])=O)[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][N:55]([C:58](=[O:70])[C:59]2[CH:64]=[C:63]([F:65])[CH:62]=[CH:61][C:60]=2[C:66]([F:69])([F:68])[F:67])[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[F:65][C:63]1[CH:62]=[CH:61][C:60]([C:66]([F:68])([F:67])[F:69])=[C:59]([CH:64]=1)[C:58]([N:55]1[CH2:56][CH2:57][N:52]([C:50](=[O:51])[CH2:49][NH:48][C:23]([C:20]2[CH:19]=[C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][CH3:10])[NH:22][N:21]=2)=[O:25])[CH2:53][CH2:54]1)=[O:70]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669531292-Amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]ethanone hydrochlorideHCID 178489299HCID 178489299, compound

Product 1

HCID 178489297HCID 178489297, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (166 mg, 0.22 mL, 1.28 mmol) was added to a stirred solution of 5-(2-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid (70 mg, 0.32 mmol) in DMF (2 mL). HOBT (55 mg, 0.4 mmol) and EDCI (77 mg, 0.4 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (119 mg, 0.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated out to afford 70 mg (40.9% yield) of 5-(2-methoxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 94.72%. 1H NMR (DMSO-d6): δ 13.45 (s, 1H), 8.0 (m, 1H), 7.88 (m, 1H), 7.7 (d, 1H), 7.46 (m, 2H), 7.4 (m, 1H), 7.1 (d, 1H), 7.0 (m, 2H), 4.32 (d, 2H), 3.86 (s, 3H), 3.64 (m, 1H), 3.5 (m, 3H), 3.4 (m, 1H), 3.1 (m, 3H).

Workup

  1. filtrationfiltered the solid
  2. customprecipitated out

Sources & evidence

ORD record
ord-230cd6f1c8c14a2da1b2d78966437383
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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