1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523551, compound

HRID 1177920Notes

Reaction equation

HRID 1177920 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[NH:21][N:20]=[C:19]([C:22]([OH:24])=O)[CH:18]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:69])[C:58]2[CH:63]=[C:62]([F:64])[CH:61]=[CH:60][C:59]=2[C:65]([F:68])([F:67])[F:66])[CH2:53][CH2:52]1)=[O:50]>CN(C=O)C.O>[F:64][C:62]1[CH:61]=[CH:60][C:59]([C:65]([F:67])([F:66])[F:68])=[C:58]([CH:63]=1)[C:57]([N:54]1[CH2:55][CH2:56][N:51]([C:49](=[O:50])[CH2:48][NH:47][C:22]([C:19]2[CH:18]=[C:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[F:10])[NH:21][N:20]=2)=[O:24])[CH2:52][CH2:53]1)=[O:69]

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 178524114HCID 178524114, compound

Product 1

HCID 178523551HCID 178523551, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (123 mg, 0.16 mL, 0.95 mmol) was added to a stirred solution of 5-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid (56 mg, 0.27 mmol) in DMF (2 mL). HOBT (39 mg, 0.28 mmol) and EDCI (55 mg, 0.28 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 (100 mg, 0.27 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitate. The solid was purified by recrystallisation from a mixture of ethyl acetate and hexane to afford 65 mg (33.16% yield) of 5-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide. LCMS Purity: 97.49%. 1H NMR (DMSO-d6): δ 13.6 (s, 1H), 7.7 (m, 4H), 7.6 (m, 1H), 7.38 (m, 3H), 7.1 (m, 2H), 6.98 (m, 4H), 4.5 (m, 1H), 4.0 (m, 1H), 3.2 (m, 2H), 2.9 (m, 2H), 1.91 (m, 1H), 1.65 (m, 2H), 1.4 (m, 2H).

Workup

  1. filtrationfiltered the solid precipitate
  2. customThe solid was purified by recrystallisation from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-7a29fc19d1274d318439ab94843ae8cf
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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