Triethylamine → HCID 86621039, compound

HRID 2243360Notes

Reaction equation

HRID 2243360 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.C1[C:35]2[C:34](=[O:36])[C:33]3C(=CC=CC=3)C=2C(C(Cl)=O)=CC=1>ClCCl>[CH:34]([O:36][CH:12]([CH3:11])[CH3:13])([CH3:35])[CH3:33].[NH2:15][C:10]1[CH:9]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:13]=[CH:12][C:11]=1[NH-:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6101429-Fluorenone-4-carbonyl chlorideHCID 27635454-(4-Methylpiperazino)-1,2-benzenediamine

Product 2

HCID 7914Diisopropyl EtherHCID 86621039HCID 86621039, compoundYield 390.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 2.06 g of 4-(4-methylpiperazin-1-yl)benzene-1,2-diamine, 2.85 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 4 g of [2-amino-4-(4-methylpiperazin-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. customAfter purification by flash chromatography on silica gel (40-63 μm)
  2. washeluting with a mixture of dichloromethane and methanol (95/5 by volume)

Sources & evidence

ORD record
ord-23c36263e9a242a481953e7f13dd401b
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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