Reaction #2330538

Reaction equation

triethylamine

9H-fluoren-9-one-4-carboxylic acid chloride

4-fluoro-5-(4-methylperhydro-1,4-diazepin-1-yl)benzene-1,2-diamine

→

[2-amino-5-fluoro-4-(4-methylperhydro-1,4-diazepin-1-yl)phenyl]amide

Yield 66.7%

diisopropyl ether

Solvents

dichloromethane

Conditions

Workup

1. 1
   Othercan be prepared
2. 2
   OtherAfter purification by flash chromatography on silica gel (40-63 μm)
3. 3
   Washeluting with a mixture of dichloromethane and methanol (95/5 by volume)

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 2.86 g of 4-fluoro-5-(4-methylperhydro-1,4-diazepin-1-yl)benzene-1,2-diamine, which can be prepared according to J. Het. Chem. 2005, 42(1), 67-71, 2.81 ml of triethylamine and 2.427 g of 9H-fluoren-9-one-4-carboxylic acid chloride in 50 ml of dichloromethane for 20 hours at room temperature. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (95/5 by volume), then formation of a paste with diisopropyl ether, in this way we obtain 950 mg of [2-amino-5-fluoro-4-(4-methylperhydro-1,4-diazepin-1-yl)phenyl]amide of 9-oxo-9H-fluorene-4-carboxylic acid, in the form of an orange powder, which is used as it is in the following stage, with the following characteristics:

Source