Water → 6-Phenyl-hexanoic acid (3-cyano-pyridin-2-yl)-amide

HRID 2100461Notes

Reaction equation

HRID 2100461 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>C(Cl)Cl.N1C=CC=CC=1>[C:8]([C:7]1[C:2]([NH:1][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)#[N:9]

Participants

6

Reactant 3

HCID 962WaterHCID 8182592-Amino-3-cyanopyridineHCID 135978376-Phenylhexanoyl chloride

Product 1

HCID 866165906-Phenyl-hexanoic acid (3-cyano-pyridin-2-yl)-amideYield 73%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 2-amino-3-cyanopyridine [24517-64-4] (200 mg, 1.7 mmol) in CH2Cl2 (3 ml) and pyridine (3 ml) was added a solution of 6-phenylhexanoic acid chloride (1.5 eq) in CH2Cl2 (1 ml) and the reaction mixture was stirred overnight at ambient temperature. Water was added, the phases were separated and the pH of the inorganic layer was adjusted (pH 7). The inorganic phase was extracted with EtOAc (3 times), the combined organic layers were washed with brine, dried over Na2SO4, filtrated and concentrated in vacuo. Trituration from diethyl ether yielded 6-phenyl-hexanoic acid (3-cyano-pyridin-2-yl)-amide 360 mg (73%) as a white solid, MS (m/e): 294.3 [M+H+].

Workup

  1. customthe phases were separated
  2. extractionThe inorganic phase was extracted with EtOAc (3 times)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a15ca65caf764f059a0a301568591096
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

Loading…