Triethylamine → [2-Amino-4-fluoro-5-(4-methyl piperazin-1-yl)phenyl]amide

HRID 2243364Notes

Reaction equation

HRID 2243364 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:15])=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.C(N(CC)CC)C.C1[C:36]2[C:35](=[O:37])[C:34]3C(=CC=CC=3)C=2C(C(Cl)=O)=CC=1>ClCCl>[CH:35]([O:37][CH:6]([CH3:5])[CH3:7])([CH3:36])[CH3:34].[NH2:16][C:4]1[CH:3]=[C:2]([F:1])[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][C:5]=1[NH-:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6101429-Fluorenone-4-carbonyl chlorideHCID 106567604-Fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine

Product 2

HCID 7914Diisopropyl EtherHCID 131727960[2-Amino-4-fluoro-5-(4-methyl piperazin-1-yl)phenyl]amideYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 2.69 g of 4-fluoro-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine, which can be prepared according to J. Het. Chem. 2005, 42(1), 67-71, 2.82 ml of triethylamine and 2.43 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), and then formation of a paste with diisopropyl ether, in this way we obtain 1 g of [2-amino-4-fluoro -5-(4-methyl piperazin-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:

Workup

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

Sources & evidence

ORD record
ord-b4d0ec55a7094c4b8087e073fbb881e6
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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