Triethylamine → HCID 10136942, compound

HRID 1935249Notes

Reaction equation

HRID 1935249 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:8]1([CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[C:15](O)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.O.C(Cl)(Cl)(Cl)Cl>[CH:8]1([CH2:13][CH:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[C:15]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 104392-AminopyridineHCID 11776TriphenylphosphineHCID 22467935HCID 22467935, compound

Product 1

HCID 10136942HCID 10136942, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-aminopyridine (25 mg, 0.26 mmol) in acetonitrile (500 μL) was treated with 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid (75 mg, 0.22 mmol), triphenylphosphine (63 mg, 0.24 mmol), triethylamine (91 μL, 0.66 mmol), and carbon tetrachloride (300 μL). The resulting reaction mixture was stirred at 25° C. for 15 h. The cloudy reaction mixture was diluted with water and then extracted with methylene chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded impure 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-N-pyridin-2-yl-propionamide. Repurification by flash chromatography (Merck Silica gel 60, 230-400 mesh, 100% methylene chloride) afforded pure 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-N-pyridin-2-yl-propionamide. (40 mg, 43%) as a white foam: mp 73-77° C.; EI-HRMS m/e calcd for C29H28N2O (M+) 420.2202, found 420.2003.

Workup

  1. customThe resulting reaction mixture
  2. customThe cloudy reaction mixture
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-144ac5bb00ac46b8a60864f8aa005008
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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