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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Methyl-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1177890
Notes
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Reaction equation

HRID 1177890 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][C:11]1[O:15][N:14]=[C:13]([C:16]([OH:18])=O)[CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:41][CH2:42][C:43]([N:45]1[CH2:50][CH2:49][N:48]([C:51](=[O:62])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]([F:61])([F:60])[F:59])[CH2:47][CH2:46]1)=[O:44]>CN(C=O)C.O>[O:44]=[C:43]([N:45]1[CH2:46][CH2:47][N:48]([C:51](=[O:62])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]([F:61])([F:60])[F:59])[CH2:49][CH2:50]1)[CH2:42][NH:41][C:16]([C:13]1[CH:12]=[C:11]([CH3:10])[O:15][N:14]=1)=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 59559639
5-Methyl-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
Yield 59.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (82.66 mg, 0.09 mL, 0.63 mmol) was added to a stirred solution of 5-methyl-isoxazole-3-carboxylic acid (32.52 mg, 0.25 mmol) in DMF (2 mL). HOBT (34.53 mg, 0.25 mmol) and EDCI (48.9 mg, 0.25 mol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (75 mg, 0.21 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using 60-120 silica gel and 80% EtOAC in hexane as eluent) to afford 53 mg (58.62% yield) of 5-methyl-isoxazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 88.47%. 1H NMR (DMSO-d6): δ 8.55 (s, 1H), 7.88-7.74 (m, 2H), 7.74-7.62 (m, 1H), 7.6-7.5 (s, 1H), 6.75 (s, 1H), 4.22-4.4 (dd, 2H), 3.8-3.64 (m, 2H), 3.64-3.52 (s, 3H), 3.5-3.36 (m, 3H), 3.22-3.0 (m, 3H), 2.48-2.44 (s, 3H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using 60-120 silica gel and 80% EtOAC in hexane as eluent)

Sources & evidence

ORD record
ord-7388a9950adb4b8d9939ff799faa15c0
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842696B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes