4-Fluoro-5-morpholin-4-ylbenzene-1,2-diamine → HCID 178514216, compound

HRID 2243339Notes

Reaction equation

HRID 2243339 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:5]([F:14])=[CH:4][C:3]=1[NH2:15].C1C=[CH:18][C:19](=[O:32])[C:20]2C=1C(C(Cl)=O)=C1C=2C=CC=C1>ClCCl.O1CCCC1.C(N(CC)CC)C>[CH:2]([O:32][CH:19]([CH3:18])[CH3:20])([CH3:7])[CH3:3].[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[C:5]([F:14])=[CH:4][C:3]=1[NH-:15]

Participants

7

Reactant 2

HCID 15103004-Fluoro-5-morpholin-4-ylbenzene-1,2-diamineHCID 87540947Fluoren-4-one-9-carboxylic acid chloride

Product 2

HCID 7914Diisopropyl EtherHCID 178514216HCID 178514216, compoundYield 294.7%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

The procedure used in stage 1 of Example 1 is followed, but starting from 1.5 g of 1,2-diamino-4-fluoro-5-morpholino-benzene in 50 ml of dichloromethane and 15 ml of tetrahydrofuran, 1.95 ml of triethylamine and 1.7 g of fluoren-4-one-9-carboxylic acid chloride. After stirring for 20 hours at room temperature, the precipitate that formed is filtered off, and washed with dichloromethane, with water, then with a 10% saturated aqueous solution of sodium hydrogen carbonate and, finally, with water. After formation of a paste with diisopropyl ether, in this way we obtain 2.2 g of (2-amino-5-fluoro-4-morpholinophenyl)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. customthe precipitate that formed
  2. filtrationis filtered off
  3. washwashed with dichloromethane, with water

Sources & evidence

ORD record
ord-3ad9cf5f46f042e08e50f75bf79da58c
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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