Cyclopentanecarbonyl chloride → HCID 86758787, compound

HRID 1634212Notes

Reaction equation

HRID 1634212 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[CH:4]=1.[CH:11]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[NH2:10][C:5]1[CH:4]=[C:3]([CH2:2][NH:1][C:16]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:17])[CH:8]=[C:7]([NH2:9])[N:6]=1

Participants

5

Reactant 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 18677512HCID 18677512, compound

Product 1

HCID 86758787HCID 86758787, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 205.6 mg (1.49 mmol) 4-aminomethyl-pyridine-2,6-diamine in 5 ml pyridine was treated with 198 mg (1.49 mmol) cyclopentane carboxylic acid chloride and a catalytic amount 4-dimethylaminopyridine and stirred for 2.5 h at room temperature. The mixture was evaporated to dryness and the residue was purified by column chromatography on silica eluting with dichloromethane/methanol 9/1 to yield 93 mg (26%) of the title compound.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by column chromatography on silica eluting with dichloromethane/methanol 9/1

Sources & evidence

ORD record
ord-cbcc498968cc455db52e33abc5f7a1f1
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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