1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → ethyl 3-[3-phenyl-1-[3-(2-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350140Notes

Reaction equation

HRID 350140 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:10][N:11]([CH2:13]C2C=CC(C(O)=O)=CC=2)[CH:12]=1)=[O:5])[CH3:2].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][NH2:36].[OH2:37].ON1[C:43]2[CH:44]=CC=[CH:47][C:42]=2N=N1.CCN=C=N[CH2:53][CH2:54][CH2:55]N(C)C>O.CN(C)C=O>[C:23]1([C:9]2[C:8]([CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:12][N:11]([CH2:13][C:42]3[CH:43]=[CH:44][CH:55]=[C:54]([C:53]([NH:36][CH2:35][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=4)=[O:37])[CH:47]=3)[N:10]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 195092-PyridinemethanamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 694228324-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid

Product 1

HCID 23025042ethyl 3-[3-phenyl-1-[3-(2-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionateYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid (300 mg), 2-picolylamine (95 mg), 1-hydroxybenzotriazole monohydrate (130 mg), WSC (170 mg), and N,N-dimethylformamide (10 ml) was stirred at room temperature for 2.5 days. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-phenyl-1-[3-(2-picolylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (200 mg, yield: 54%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-methanol (50:1, volume ratio).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c51d311a65fb42a598c7a05400f82bfa
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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