2-Aminopyridine → ethyl 3-[3-phenyl-1-[3-(2-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate

HRID 350142Notes

Reaction equation

HRID 350142 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]=CC(C(O)=O)=[CH:16][CH:15]=2)[CH:12]=1)=[O:5])[CH3:2].N[C:30]1[CH:35]=CC=CN=1.O.[OH:37]N1C2C=CC=CC=2N=N1.[CH3:47][CH2:48][N:49]=[C:50]=[N:51][CH2:52][CH2:53][CH2:54]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:14]3[CH:15]=[CH:16][CH:54]=[C:53]([C:52]([NH:51][C:50]4[CH:30]=[CH:35][CH:47]=[CH:48][N:49]=4)=[O:37])[CH:22]=3)[N:10]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 104392-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 23024837ethyl 3-[3-phenyl-1-[3-(2-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionateYield 41.6%

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-aminopyridine (120 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 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-pyridylaminocarbonyl)benzyl]-1H-pyrazol-4-yl]propionate (200 mg, yield: 40%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (5:1, 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 sodium chloride solution, and dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-254ca7dc27c349f8b3a0489d8583fb47
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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