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

HRID 350144Notes

Reaction equation

HRID 350144 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][C:14]2[CH:22]=[CH:21][C:17](C(O)=O)=[CH:16][CH:15]=2)[CH:12]=1)=[O:5])[CH3:2].[N:29]1[CH:34]=CC=C[C:30]=1CCN.[OH2:38].O[N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.CCN=C=NCCCN(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:14]3[CH:22]=[CH:21][CH:17]=[C:16]([C:34]([NH:29][CH2:30][CH2:43][C:48]4[CH:47]=[CH:46][CH:45]=[CH:44][N:40]=4)=[O:38])[CH:15]=3)[N:10]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 759192-PyridineethanamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 694228324-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid

Product 1

HCID 23024725ethyl 3-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionateYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid (400 mg), 2-(2-pyridyl)ethylamine (170 mg), 1-hydroxybenzotriazole monohydrate (200 mg), WSC (250 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 bicarbonate solution, 1 N hydrochloric acid, then, with saturated aqueous sodium chloride solution, and dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-phenyl-1-[3-[2-(2-pyridyl)ethylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (460 mg, yield: 87%) 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 bicarbonate solution, 1 N hydrochloric acid
  3. dry with materialwith saturated aqueous sodium chloride solution, and dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bad1c88abd9c4f5dad34ef959708a582
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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