Nitrogen → N-(piperidin-1-yl)-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide

HRID 19758

Reaction equation

HRID 19758 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][C:10]([C:19](O)=[O:20])=[N:9]2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:33]2[CH:34]=[CH:35][CH:36]=C[C:32]=2[N:31]=[N:30]1.NN1CCCCC1.N#N>C(#N)C>[N:31]1([NH:30][C:19]([C:10]2[CH2:11][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)=[O:20])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 166581-AminopiperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 237308081-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 11646653N-(piperidin-1-yl)-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part D: To a stirred suspension of 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylic acid (1.50 gram, 5 mmol) in anhydrous acetonitrile (40 ml) is successively added N-diisopropylethylamine (DIPEA) (1.92 ml, 11 mmol), O-benzotriazol-1-yl-N,N, N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (2.08 g, 5.5 mmol) and 1-aminopiperidine (0.59 ml, 5.5 mmol) and the resulting mixture is reacted at room temperature for 16 hours in a N2 atmosphere. The mixture is concentrated and added to a mixture of ethyl acetate and aqueous NaHCO3. The Ethyl acetate layer is collected, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is recrystallised from acetonitrile to give N-(piperidin-1-yl)-1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxamide (compound 1), 1.34 gram, 70% yield). Melting point: 189-192° C.

Workup

  1. concentrationThe mixture is concentrated
  2. additionadded to a mixture of ethyl acetate and aqueous NaHCO3
  3. customThe Ethyl acetate layer is collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is recrystallised from acetonitrile

Sources & evidence

ORD record
ord-4c9dd9087c4b4a4b892f5151baa6d2c4
Source dataset
uspto-grants-2010_06
Patent number
US07745476B2

Linked notes

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