2-Aminopyridine → HCID 22467934, compound

HRID 1935241Notes

Reaction equation

HRID 1935241 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([CH:7]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:8](O)=[O:9])=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=1>CN(C)C=O>[C:1]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:2]=[CH:3][C:4]([CH:7]([CH2:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[C:8]([NH:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224679232-Biphenyl-4-yl-3-cyclopentylpropionic acid

Product 1

HCID 22467934HCID 22467934, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-biphenyl-4-yl-3-cyclopentylpropionic acid (300 mg, 1.02 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (386 mg, 1.02 mmol), N,N-diisopropylethylamine (220 μL, 1.22 mmol), and 2-aminopyridine (144 mg, 1.53 mmol) in dry N,N-dimethylformamide (5 ml) was stirred at 25° C. under nitrogen for 15 h. The reaction mixture was partitioned between water and ethyl acetate, and the layers were separated. The organic layer was washed with a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 2/1 hexanes/ethyl acetate) afforded 2-biphenyl-4-yl-3-cyclopentyl-N-pyridin-2-yl-propionamide (79 mg, 21%) as a white solid: mp 57-59° C.; EI-HRMS m/e calcd for C25H26NO (M+) 370.2045, found 370.2049.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe layers were separated
  3. washThe organic layer was washed with a 1N aqueous hydrochloric acid solution, water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-060af8e6df0547ddb166620107abe169
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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