1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523550, compound

HRID 1178141Notes

Reaction equation

HRID 1178141 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:27])([F:26])[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.[NH2:50][CH2:51][C:52]([N:54]1[CH2:59][CH2:58][N:57]([C:60](=[O:72])[C:61]2[CH:66]=[C:65]([F:67])[CH:64]=[CH:63][C:62]=2[C:68]([F:71])([F:70])[F:69])[CH2:56][CH2:55]1)=[O:53]>CN(C=O)C.O>[F:67][C:65]1[CH:64]=[CH:63][C:62]([C:68]([F:70])([F:69])[F:71])=[C:61]([CH:66]=1)[C:60]([N:57]1[CH2:58][CH2:59][N:54]([C:52](=[O:53])[CH2:51][NH:50][C:23]([C:20]2[CH:19]=[C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11]([F:10])([F:27])[F:26])[NH:22][N:21]=2)=[O:25])[CH2:55][CH2:56]1)=[O:72]

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 1785241123-(2-(trifluoromethyl)phenyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 178523550HCID 178523550, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (124 mg, 0.16 mL, 0.95 mmol) was added to a stirred solution of 5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid (70 mg, 0.27 mmol) in DMF (2 mL). HOBT (43 mg, 0.31 mmol) and EDCI (60 mg, 0.31 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (101 mg, 0.27 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitate. The solid was purified by dissolving in DCM and washed with 1.2N HCl. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 57 mg (36.77% yield) of 5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 93.30%. 1H NMR (DMSO-d6): δ 13.6 (s, 1H), 8.1 (m, 1H), 7.9 (m, 2H), 7.5 (m, 21H), 7.5 (m, 6H), 6.79 (s, 1H), 4.1 (d, 2H), 3.5 (m, 7H), 3.0 (m, 3H).

Workup

  1. filtrationfiltered the solid precipitate
  2. customThe solid was purified
  3. dissolutionby dissolving in DCM
  4. washwashed with 1.2N HCl
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-acf57c60f91b4df28458c2f29bf4b26b
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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