1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-ethyl}-amide

HRID 1093844Notes

Reaction equation

HRID 1093844 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[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.[F:49][C:50]([F:64])([F:63])[C:51]1[CH:52]=[C:53]([CH:60]=[CH:61][CH:62]=1)[O:54][CH:55]1[CH2:59][CH2:58][NH:57][CH2:56]1>CN(C=O)C.O>[O:27]=[C:25]([N:57]1[CH2:58][CH2:59][CH:55]([O:54][C:53]2[CH:60]=[CH:61][CH:62]=[C:51]([C:50]([F:49])([F:64])[F:63])[CH:52]=2)[CH2:56]1)[CH2:24][NH:23][C:21]([C:18]1[CH:17]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:20][N:19]=1)=[O:22]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 183371713-[3-(Trifluoromethyl)phenoxy]pyrrolidineHCID 178525878HCID 178525878, compound

Product 1

HCID 1785235045-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-ethyl}-amideYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (167.7 mg, 1.29 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (106 mg, 0.43 mmol) in DMF (4 mL) followed by HOBt (70.13 mg, 0.52 mmol) and EDCI (99.5 mg, 0.52 mmol). After 2 minutes of stirring, 3-(3-trifluoromethyl-phenoxy)-pyrrolidine (100 mg, 0.43 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected to afford 122 mg (61.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-pyrrolidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 459.16, 96.52%. 1H NMR (300 MHz, DMSO-d6): δ 13.8 (s, 1H), 8.05 (bs, 1H), 7.8 (db, 2H), 7.7-7.6 (m, 7H), 7.05 (bs, 1H), 5.4 (s, 1H), 5.3 (s, 1H), 4.1 (m, 2H), 3.9 (m, 1H), 3.8-3.6 (m, 3H), 3.4 (m, 1H), 2.3-2.0 (m, 2H).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customthe precipitate was collected

Sources & evidence

ORD record
ord-1ab4f5c258b4430ea58c672f585354b9
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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