3-Aminopyridine → ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350146Notes

Reaction equation

HRID 350146 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].NC1[CH:31]=[N:32][CH:33]=CC=1.O.[OH:37]N1C2C=CC=CC=2N=N1.CCN=C=N[CH2:52][CH2:53][CH2:54][N:55]([CH3:57])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:15]=[CH:16][CH:17]=[C:21]([C:31]([NH:32][C:33]4[CH:57]=[N:55][CH:54]=[CH:53][CH:52]=4)=[O:37])[CH:22]=3)[N:10]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 694228324-[4-(2-ethoxycarbonylethyl)-3-phenyl-1H-pyrazol-1-ylmethyl]benzoic acid

Product 1

HCID 23024973ethyl 3-[3-phenyl-1-[3-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionateYield 58.3%

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), 3-aminopyridine (160 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-(3-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (280 mg, yield: 56%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-methanol (50:1, volume ratio). Melting point: 111–112° C.

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-78be06b1d96445d792058273c55dfd1f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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