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Diisopropylethylamine → 4-Phenyl-pyrazole-1-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1178109
Notes
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Reaction equation

HRID 1178109 reaction equation
Cl.[C:2]1([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.Cl.[NH2:35][CH2:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45](=[O:56])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]([F:55])([F:54])[F:53])[CH2:41][CH2:40]1)=[O:38]>C(Cl)Cl.O>[O:38]=[C:37]([N:39]1[CH2:40][CH2:41][N:42]([C:45](=[O:56])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]([F:55])([F:53])[F:54])[CH2:43][CH2:44]1)[CH2:36][NH:35][C:23]([N:10]1[CH:9]=[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=[N:11]1)=[O:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 665923304-phenyl-1H-pyrazole hydrochlorideHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

Product 1

HCID 251655334-Phenyl-pyrazole-1-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide
Yield 32.97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 4-Phenyl-1H-pyrazole hydrochloride salt (prepared by the method described above)(44 mg, 0.3 mmol), DIPEA (88 mg, 0.119 ml, 0.685 mmol) and DCM (2 ml) was added to a stirred solution of triphosgene (36 mg, 0.12 mmol) in DCM (1 mL) at room temperature. After 30 minutes, to the above solution, a mixture of 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method described above)(108 mg, 0.3 mmol), DIPEA (88 mg, 0.119 ml, 0.685 mmol) and DCM (2 ml) was added and the resulting mixture was stirred at room temperature for 30 minutes. 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 silica gel of 60-120 mesh and 30-70% EtOAc in Hexane as eluent) to afford 48.8 mg (32.97% yield) 4-Phenyl-pyrazole-1-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 97.25%. 1H NMR (CDCl3): δ 8.48-8.4 (d, 1H), 8.04-7.98 (bs, 1H), 7.96-7.92 (s, 1H), 7.8-7.74 (d, 1H), 7.7-7.58 (m, 2H), 7.56-7.5 (d, 2H), 7.44-7.1 (m, 4H), 4.38-4.3 (d, 2H), 4.28-4.2 (t, 1H), 4.1-4.0 (bs, 1H), 3.82-3.66 (m, 2H), 3.64-3.5 (m, 2H), 3.46-3.38 (t, 1H),), 3.32-3.2 (s, 2H).

Workup

  1. customprepared by the method
  2. customprepared by the method
  3. additionwas added
  4. extractionthe product was extracted with EtOAc
  5. washthe organic layer was washed with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto get the residue
  9. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 30-70% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-0a1def37a07249e189cfd964ab461502
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